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Chemical Structure| 81477-94-3 Chemical Structure| 81477-94-3
Chemical Structure| 81477-94-3

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CAS No.: 81477-94-3

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Synonyms: N-(Diphenylmethylene)glycine tert-butyl ester

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Product Details of N-(Diphenylmethylene)glycine tert-butyl ester

CAS No. :81477-94-3
Formula : C19H21NO2
M.W : 295.38
SMILES Code : O=C(OC(C)(C)C)C/N=C(C1=CC=CC=C1)\C2=CC=CC=C2
Synonyms :
N-(Diphenylmethylene)glycine tert-butyl ester
MDL No. :MFCD00134280
InChI Key :YSHDPXQDVKNPKA-UHFFFAOYSA-N
Pubchem ID :688171

Safety of N-(Diphenylmethylene)glycine tert-butyl ester

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

Application In Synthesis of N-(Diphenylmethylene)glycine tert-butyl ester

* 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 [ 81477-94-3 ]

[ 81477-94-3 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 81477-94-3 ]
  • [ 81998-05-2 ]
  • (R)-2-(Benzhydrylidene-amino)-3-(4'-methyl-[2,2']bipyridinyl-4-yl)-propionic acid tert-butyl ester [ No CAS ]
  • [ 402563-43-3 ]
  • 2
  • [ 3913-23-3 ]
  • [ 81477-94-3 ]
  • 2-(benzhydrylidene-amino)-3-(2-methoxy-5-nitro-phenyl)-propionic acid <i>tert</i>-butyl ester [ No CAS ]
  • 3
  • [ 81477-94-3 ]
  • [ 91229-86-6 ]
  • 4
  • [ 101990-45-8 ]
  • [ 81477-94-3 ]
  • [ 462123-60-0 ]
YieldReaction ConditionsOperation in experiment
With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide; In dichloromethane; at -78 - 20℃; This, together with tert-butyl 2- (diphenylmethyleneamino)acetate (4.71 g) and (2S,4S,5R)-2-((R)-allyloxy(quinolin-4- yl)methyl)-l-(anthracen-9-ylmethyl)-5-vinyl-l-azoniabicyclo[2.2.2]octane bromide (1.073 g)5 was dissolved in DCM (100 mL) and the solution was cooled to -78 0C under nitrogen. 2-tert- Butylimino-2-diethylamino-l,3-dimethyl-perhydro-l,3,2-diazaphosphorine (5 mL) was added drop wise over 5 min and the mixture was stirred at -78 0C for 7 h then allowed to reach RT overnight. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and water. The ethyl acetate was washed with brine, dried over magnesium sulfate, io filtered and concentrated in vacuo.
  • 5
  • [ 407-97-6 ]
  • [ 81477-94-3 ]
  • tert-butyl (RS)-2-((diphenylmethylene)amino)-7-fluoroheptanoate [ No CAS ]
  • 6
  • [ 192702-01-5 ]
  • [ 81477-94-3 ]
  • (S)-tert-butyl N-(diphenylmethylene)-(3-chloro-4-fluorophenyl)alaninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With C37H37N2O(1+)*Br(1-); potassium hydroxide; In chloroform; water; toluene; at -40℃; for 72h; A 10 mL reactiontube was charged with 2 (30 mg, 0.1 mmol), 3,5-dichlorobenzyl bromide (119 mg, 0.5 mmol, 5 equivalent), catalyst 1f (6 mg, 0.01 mmol, 0.1 equivalent) and toluene and CHCl3 (1.5 mL, 2:1 v/v),and the mixture was cooled to 40 C. After the mixture was stirred for 10 min, 50% aq. KOH (28L, 0.1 mmol, 5 equivalent) was added, and the whole reaction mixture was stirred at 40 C for72 h before being allowed to warm to ambient temperature. The reaction was quenched by addingH2O (2 mL), and the resulting mixture was extracted with EtOAc (3 10 mL). The combined extractswere washed with brine (10 mL) and dried (anhydrous Na2SO4), and the crude product was purifiedby flash column chromatography (eluting with hexane/EtOAc, 50:1) to afford 4a (43 mg, 95% yield)as light yellow liquid. 97% ee; []20D 178.8 (c = 1.0, CH2Cl2); 1H-NMR (400 MHz, CDCl3): 7.57 (s,1H), 7.55 (d, J = 1.4 Hz, 1H), 7.40-7.29 (m, 6H), 7.16 (t, J = 1.7 Hz, 1H), 6.95 (d, J = 1.7 Hz, 2H), 6.76(d, J = 6.1 Hz, 2H), 4.12 (dd, J = 8.9, 4.6 Hz, 1H), 3.19-3.08 (m, 2H), 1.45 (s, 9H); 13C-NMR (100 MHz,CDCl3): 171.1, 170.2, 141.7, 139.2, 136.1, 134.4, 130.3, 128.7, 128.6, 128.3, 128.3, 128.0, 127.6, 126.4, 81.6,66.9, 38.9, 28.0; HRMS (ESI, positive): Calcd. for C26H26Cl2NO2 [M + H]+ 454.1335, found: 454.1333.HPLC analysis: Daicel Chiralcel OD-H, n-hexane/isopropanol = 95:5, flow rate = 0.5 mL/min.
  • 7
  • [ 192702-01-5 ]
  • [ 81477-94-3 ]
  • (R)-tert-butyl N-(diphenylmethylene)-(3-chloro-4-fluorophenyl)alaninate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With C37H37N2O(1+)*Br(1-); potassium hydroxide; In chloroform; water; toluene; at -40℃; for 72h; A 10 mL reactiontube was charged with 2 (30 mg, 0.1 mmol), 3,5-dichlorobenzyl bromide (119 mg, 0.5 mmol, 5 equivalent), catalyst 1f (6 mg, 0.01 mmol, 0.1 equivalent) and toluene and CHCl3 (1.5 mL, 2:1 v/v),and the mixture was cooled to 40 C. After the mixture was stirred for 10 min, 50% aq. KOH (28L, 0.1 mmol, 5 equivalent) was added, and the whole reaction mixture was stirred at 40 C for72 h before being allowed to warm to ambient temperature. The reaction was quenched by addingH2O (2 mL), and the resulting mixture was extracted with EtOAc (3 10 mL). The combined extractswere washed with brine (10 mL) and dried (anhydrous Na2SO4), and the crude product was purifiedby flash column chromatography (eluting with hexane/EtOAc, 50:1) to afford 4a (43 mg, 95% yield)as light yellow liquid. 97% ee; []20D 178.8 (c = 1.0, CH2Cl2); 1H-NMR (400 MHz, CDCl3): 7.57 (s,1H), 7.55 (d, J = 1.4 Hz, 1H), 7.40-7.29 (m, 6H), 7.16 (t, J = 1.7 Hz, 1H), 6.95 (d, J = 1.7 Hz, 2H), 6.76(d, J = 6.1 Hz, 2H), 4.12 (dd, J = 8.9, 4.6 Hz, 1H), 3.19-3.08 (m, 2H), 1.45 (s, 9H); 13C-NMR (100 MHz,CDCl3): 171.1, 170.2, 141.7, 139.2, 136.1, 134.4, 130.3, 128.7, 128.6, 128.3, 128.3, 128.0, 127.6, 126.4, 81.6,66.9, 38.9, 28.0; HRMS (ESI, positive): Calcd. for C26H26Cl2NO2 [M + H]+ 454.1335, found: 454.1333.HPLC analysis: Daicel Chiralcel OD-H, n-hexane/isopropanol = 95:5, flow rate = 0.5 mL/min.
 

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