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Chemical Structure| 42538-40-9 Chemical Structure| 42538-40-9

Structure of H-Phe(2-Br)-OH
CAS No.: 42538-40-9

Chemical Structure| 42538-40-9

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Product Details of [ 42538-40-9 ]

CAS No. :42538-40-9
Formula : C9H10BrNO2
M.W : 244.09
SMILES Code : O=C(O)[C@@H](N)CC1=CC=CC=C1Br
MDL No. :MFCD03092958
InChI Key :JFVLNTLXEZDFHW-QMMMGPOBSA-N
Pubchem ID :193338

Safety of [ 42538-40-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 42538-40-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 13
Num. arom. heavy atoms 6
Fraction Csp3 0.22
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 53.2
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

63.32 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.45
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

-0.72
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.4
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

-0.39
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

1.55
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.66

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.04
Solubility 22.1 mg/ml ; 0.0905 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-0.13
Solubility 179.0 mg/ml ; 0.735 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.72
Solubility 0.461 mg/ml ; 0.00189 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-8.3 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 2.13

Application In Synthesis of [ 42538-40-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 42538-40-9 ]

[ 42538-40-9 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 42538-40-9 ]
  • [ 55135-66-5 ]
  • [ 147912-84-3 ]
  • 3
  • [ 42538-40-9 ]
  • [ 501-53-1 ]
  • Z-L-Phe(2Br) [ No CAS ]
  • 4
  • [ 63-91-2 ]
  • [ 42538-40-9 ]
  • [ 24250-84-8 ]
  • 5
  • [ 42538-40-9 ]
  • [ 458528-69-3 ]
  • 6
  • [ 42538-40-9 ]
  • [ 79815-20-6 ]
YieldReaction ConditionsOperation in experiment
95.9% With potassium carbonate;copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 80 - 100℃; for 3.5 - 4h;Product distribution / selectivity; Example 1 (S)-2,3-dihydro-1 H-indole-2-carboxylic acid: Conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> with 2 molpercent CuCl in NMP at 100°C A flask was charged successively with 366 mg (1.5 mmol) <strong>[42538-40-9](S)-2-bromophenylalanine</strong>, 217 mg (1.6 mmol) K2CO3, 3.2 mg (0.03 mmol) CuCl and 3.2 g NMP. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 100°C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 4 hours, full conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The yield (measured in solution) of (S)-2,3-dihydro-1 H-indole-2-carboxylic acid was 95.9 percent, ee > 98.6percent.; Example 2 (S)-2,3-dihydro-1H-indole-2-carboxylic acid: Conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> with 1 molpercent CuCl in NMP at 80°C A flask was charged successively with 9.76 g (40.0 mmol) <strong>[42538-40-9](S)-2-bromophenylalanine</strong>, 5.80 g (42.0 mmol) K2CO3, 40 mg (0.4 mmol) CuCl and 40 g NMP. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 80°C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 3.5 h full conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The reaction mixture was cooled to 25°C and then 40 mL H2O and 50 mL aqueous EtOAc were added. The pH of this mixture was adjusted to 3.3 with 3.5 g 37percent aqueous HCl. The phases were separated. The H2O phase was extracted with 2 x 50 mL aqueous EtOAc. The combined organic layers were washed with 25 mL sat aqueous NaCl. Then the organic phase was concentrated. The residu was dissolved in 16 mL 5N aqueous HCl, followed by pH adjustment to 2.1 with 9.4 g 32percent aqueous NaOH. The precipitated (S)-2,3-dihydro-1H-indole-2-carboxylic acid was isolated by filtration and washed with 2 x 10 mL H2O. 3.24 g (19.8 mmol) (S)-2,3-dihydro-1 H-indole-2-carboxylic acid was found after drying. Yield 49.5percent, ee >99percent.
95.6% With potassium carbonate; In water; at 95℃; for 22h;Product distribution / selectivity; A flask was charged successively with 366 mg (1.5 mmol) <strong>[42538-40-9](S)-2-bromophenylalanine</strong>, 217 mg (1.6 mmmol) K2CO3 and 3 g H2O. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 95°C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 5h hour the conversion was approximately 37percent. After 22h full conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The reaction mixture was cooled to 25°C and analyzed by HPLC. The yield in solution of (S)-2,3-dihydro-1 H-indole-2-carboxylic acid was 95.6 percent, ee > 99percent.
81.1% With potassium carbonate;copper(l) chloride; In water; at 95℃; for 2 - 4h;Product distribution / selectivity; Example 3 (S)-2,3-dihydro-1 H-indole-2-carboxylic acid: Conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> with 2 molpercent CuCl in water at 95°C A flask was charged successively with 366 mg (1.5 mmol) <strong>[42538-40-9](S)-2-bromophenylalanine</strong>, 217 mg (1.6 mmol) K2CO3, 3 mg (0.03 mmol) CuCl and 3.4 g H2O. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 95°C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 2 hour full conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The reaction mixture was cooled to 25°C and analyzed by HPLC. The yield in solution of (S)-2,3-dihydro-1 H-indole-2-carboxylic acid was 81.1 percent, ee > 99percent.; Example 4 (S)-2,3-dihydro-1 H-indole-2-carboxylic acid: Conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> with 0.01 molpercent CuCl in water at 95°C A flask was charged successively with 4.89 g (20.0 mmol) <strong>[42538-40-9](S)-2-bromophenylalanine</strong>, 2.93 g (21.2 mmol) K2CO3, 0.2 mg CuCl (2.9 mmol) and 39.7 g H2O. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 95°C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 4h hour full conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The reaction mixture was cooled to 25°C. Then the reaction mixture was acidified with 4.47 g 5M aqueous HCI until pH = 4.4. The precipitated (S)-2,3-dihydro-1 H-indole-2-carboxylic acid was isolated by filtration and washed with 2 x 10 mL H2O. Found after drying 2.24 g (13.7 mmol) (S)-2,3-dihydro-1 H-indole-2-carboxylic acid. Yield 69percent, ee >99percent.
69% Example 4; (S)-2,3-dihydro-1 H-indole-2-carboxylic acid: Conversion of (S)-2- bromophenylalanine with 0.01 molpercent CuCI in water at 95°C EPO <DP n="30"/>; A flask was charged successively with 4.89 g (20.0 mmol) (S)-2- bromophenylalanine, 2.93 g (21.2 mmol) K2CO3, 0.2 mg CuCI (2.9 mmol) and 39.7 g H2O. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 95°C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 4h hour full conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The reaction mixture was cooled to 25°C. Then the reaction mixture was acidified with 4.47 g 5M aqueous HCI until pH = 4.4. The precipitated (S)-2,3-dihydro-1H-indole-2-carboxylic acid was isolated by filtration and washed with 2 x 10 ml_ H2O. Found after drying 2.24 g (13.7 mmol) (S)-2,3-dihydro-1H- indole-2-carboxylic acid. Yield 69percent, ee >99percent.
49.5% Example 2; (S)-2,3-dihydro-1H-indole-2-carboxylic acid: Conversion of (S)-2- bromophenylalanine with 1 molpercent CuCI in NMP at 800C; A flask was charged successively with 9.76 g (40.0 mmol) (S)-2- bromophenylalanine, 5.80 g (42.0 mmol) K2CO3, 40 mg (0.4 mmol) CuCI and 40 g NMP. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 800C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 3.5 h full conversion of (S)- 2-bromophenylalanine was found. The reaction mixture was cooled to 25°C and then 40 ml_ H2O and 50 mL aqueous EtOAc were added. The pH of this mixture was adjusted to 3.3 with 3.5 g 37percent aqueous HCI. The phases were separated. The H2O phase was extracted with 2 x 50 mL aqueous EtOAc. The combined organic layers were washed with 25 mL sat aqueous NaCI. Then the organic phase was concentrated. The residu was dissolved in 16 mL 5N HCI, followed by pH adjustment to 2.1 with 9.4 g 32percent aqueous NaOH. The precipitated (S)-2,3-dihydro-1H-indole-2- carboxylic acid was isolated by filtration and washed with 2 x 10 mL H2O. 3.24 g (19.8 mmol) (S)-2,3-dihydro-1 H-indole-2-carboxylic acid was found after drying. Yield 49.5percent, ee >99percent.
95.9%Chromat. With potassium carbonate; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 100℃; for 4h;Product distribution / selectivity; Examplei; (S)-2,3-dihydro-1H-indole-2-carboxylic acid: Conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> with 2 molpercent CuCI in NMP at 1000C; A flask was charged successively with 366 mg (1.5 mmol) (S)-2- bromophenylalanine, 217 mg (1.6 mmol) K2CO3, 3.2 mg (0.03 mmol) CuCI and 3.2 g NMP. The reactor was flushed with argon and then kept under a slow stream of argon.The reaction mixture was stirred and heated until 1000C and kept at this temperature.Samples were taken regularly and analyzed by HPLC. After 4 hours, full conversion of<strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The yield (measured in solution) of (S)-2,3- dihydro-1 H-indole-2-carboxylic acid was 95.9 percent, ee > 98.6percent.
81.1%Chromat. With potassium carbonate; copper(l) chloride; In water; at 95℃; for 2h;Product distribution / selectivity; Example 3; (S)-2,3-dihydro-1 H-indole-2-carboxylic acid: Conversion of (S)-2- bromophenylalanine with 2 molpercent CuCI in water at 95°C; A flask was charged successively with 366 mg (1.5 mmol) (S)-2- bromophenylalanine, 217 mg (1.6 mmol) K2CO3, 3 mg (0.03 mmol) CuCI and 3.4 g H2O. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 95°C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 2 hour full conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The reaction mixture was cooled to 25°C and analyzed by HPLC. The yield in solution of (S)-2,3-dihydro-1H-indole-2-carboxylic acid was 81.1 percent, ee > 99percent.
95.6%Chromat. With potassium carbonate; In water; at 95℃; for 22h;Product distribution / selectivity; Example 5; (S)-2,3-dihydro-1H-indole-2-carboxylic acid: Conversion of (S)-2- bromophenylalanine without CuCI in water at 95°C; A flask was charged successively with 366 mg (1.5 mmol) (S)-2- bromophenylalanine, 217 mg (1.6 mmmol) K2CO3 and 3 g H2O. The reactor was flushed with argon and then kept under a slow stream of argon. The reaction mixture was stirred and heated until 95°C and kept at this temperature. Samples were taken regularly and analyzed by HPLC. After 5h hour the conversion was approximately 37percent. After 22h full conversion of <strong>[42538-40-9](S)-2-bromophenylalanine</strong> was found. The reaction mixture was cooled to 25°C and analyzed by HPLC. The yield in solution of (S)-2,3-dihydro-1 H- indole-2-carboxylic acid was 95.6 percent, ee > 99percent.

  • 7
  • [ 7148-74-5 ]
  • [ 42538-40-9 ]
  • [ 882068-31-7 ]
YieldReaction ConditionsOperation in experiment
Introduce 28.8 g of <strong>[42538-40-9](S)-2-bromophenylalanine</strong>, 7.5 ml of water and 15 ml of toluene into a reactor; then bring the mixture to between 0 and 5° C. and add 25 ml of 5M sodium hydroxide solution and then a solution of 20.2 g of (2R)-2-bromopropionyl chloride in toluene, whilst keeping the temperature below 10° C. and maintaining the pH of the mixture at 10 by adding 5M sodium hydroxide solution. After stirring for a further 1 hour at 10° C., add concentrated hydrochloric acid to bring the pH of the mixture to 6. Separate off the toluene phase and then add concentrated hydrochloric acid to the aqueous phase to bring the pH to 2. The precipitate formed is then filtered off and dried to yield the title compound.
  • 11
  • [ 34973-13-2 ]
  • [ 42538-40-9 ]
  • [ 612548-09-1 ]
YieldReaction ConditionsOperation in experiment
Step A. Preparation of (2S)-3-(2-bromo-phenyl)-2-methoxycarbonylamino-propionic acid (or L-Moc-2-bromophenylalanine) 1.0 g <strong>[42538-40-9]L-2-bromophenylalanine</strong> (Peptech Corp.) is dissolved in 6 mL 1M K2CO3 followed by 0.77 g methoxycarbonyloxysuccinimide in 20 mL acetone. The resulting clear biphasic solution is stirred for 4 h, then concentrated to 10 mL. The resulting basic solution is extracted with ether and the aqueous phase rendered acidic with 6 M HCl. The oily precipitate is extracted with EtOAc (2*20 mL) and evaporated to yield 1.16 g of a clear oil which crystallizes upon standing. 1H NMR (CD3OD): delta 2.94-3.02 (m, 1H), 3.30-3.36 (m, 1H), 3.51 (s, 3H) 4.52 (t, J=7.6, 1H), 7.04 (t. J=6.8 1H), 7.20-7.26 (m, 2H), 7.52 (d, J=7.0, 2H).
  • 12
  • C34H30BrN3NiO3 [ No CAS ]
  • [ 42538-40-9 ]
  • [ 96293-17-3 ]
  • 13
  • [ 7345-79-1 ]
  • [ 42538-40-9 ]
  • (S)-3-amino-3-(2-bromophenyl)propionic acid [ No CAS ]
  • 14
  • [ 7345-79-1 ]
  • [ 267225-27-4 ]
  • [ 42538-40-9 ]
  • (S)-3-amino-3-(2-bromophenyl)propionic acid [ No CAS ]
  • 15
  • [ 7345-79-1 ]
  • [ 267225-27-4 ]
  • [ 42538-40-9 ]
  • 16
  • [ 42538-40-9 ]
  • [ 98-80-6 ]
  • C15H15NO2 [ No CAS ]
  • 17
  • [ 120240-65-5 ]
  • [ 3060-50-2 ]
  • [ 119-61-9 ]
  • [ 267225-27-4 ]
  • [ 42538-40-9 ]
YieldReaction ConditionsOperation in experiment
With C39H33N3O2*2ClH; In methanol; water; at 20℃; for 72h; General procedure: To a 5 mL vial equipped with a magnetic stirrer bar were added 3-cyclohexyl-2-oxopropanoic acid (1j) (0.0510 g, 0.30 mmol), 2,2-diphenylglycine (2) (0.0681 g, 0.30 mmol), chiral pyridoxamine 6g (0.0195 g, 0.030 mmol), and MeOH-H2O (8:2) (3.0 mL). The mixture was stirred at 20 °C for 3 days. The reaction mixture was transferred to a 25 mL round-bottom flask and MeOH was added until all the solid was dissolved. Then silica gel (0.50 g) was added. After removal of the solvent in vacuo at 20 °C, the resulting residue was submitted to column chromatography on silica gel (EtOH/ethyl acetate/25-28percent ammonia solution =100:58:16) to give compound 3j (0.0401 g, 78percent yield, 52percent ee) as a white solid. The enantiomeric excesses of 3b-k were deteremined by HPLC analysis after being converted to N-benzoyl methyl esters by treatment with thionyl chloride in methanol and subsequent reaction benzoyl chloride.7 The enantiomeric excess of 3a was deteremined by HPLC analysis after being converted to its methyl ester by treatment with CH2N2 in methanol.
  • 18
  • [ 6630-33-7 ]
  • [ 42538-40-9 ]
YieldReaction ConditionsOperation in experiment
With C39H33N3O2*2ClH; water; 2,2-diphenylglycine; In methanol; at 20℃; for 72h; General procedure: Take 5mL of the reaction bottle. Was weighed into the flask the keto acid 2a (0.046 g, 0.20 mmol), the chiral pyridoxamine catalyst 1a (0.013 g, 0.020 mmol), and 2,2-diphenylglycine 14 (0.045 g, 0.20 mmol). To the flask was added MeOH (1.6 mL) and water (0.4 mL). Adding a magnet, plug a good stopper, placed in 20°C constant temperature reaction tank reaction for 3d. The reaction was stopped. The contents of the flask were transferred to a 25 mL eggplant flask. 10 mL of methanol was added to dissolve all the solids in the flask. Silica gel (0.2 g) was added. The solvent was removed at room temperature. Dry on the column. Silica gel column chromatography gave the product amino acid 3a (0.023 g, 50percent). The ee value of 3a was obtained by HPLC analysis of its carboxymethylated derivative with an ee value of 34percent.
  • 20
  • [ 42538-40-9 ]
  • methyl (S)-3-(2-bromophenyl)-2-((2-nitrophenyl)sulfonamido)propanoate [ No CAS ]
  • 21
  • [ 42538-40-9 ]
  • C25H19BrN2O6S [ No CAS ]
  • methyl (S)-3-(2-bromophenyl)-2-(N-((1S,2S)-1-hydroxy-1,2-dihydronaphthalen-2-yl)-2-nitrophenylsulfonamido)propanoate [ No CAS ]
  • 22
  • [ 42538-40-9 ]
  • (3S,4aR,10bR)-3-(2-bromobenzyl)-4-((2-nitrophenyl)sulfonyl)-3,4,4a,10b-tetrahydro-2H-naphtho[1,2-b][1,4]oxazin-2-one [ No CAS ]
 

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