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Chemical Structure| 6456-74-2 Chemical Structure| 6456-74-2
Chemical Structure| 6456-74-2

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CAS No.: 6456-74-2

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tert-Butyl Glycinate is a glycine derivative, commonly used in peptide synthesis and drug development.

Synonyms: tert-Butyl 2-aminoacetate

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Product Details of tert-Butyl Glycinate

CAS No. :6456-74-2
Formula : C6H13NO2
M.W : 131.17
SMILES Code : CC(C)(C)OC(=O)CN
Synonyms :
tert-Butyl 2-aminoacetate
MDL No. :MFCD00038194
InChI Key :SJMDMGHPMLKLHQ-UHFFFAOYSA-N
Pubchem ID :151417

Safety of tert-Butyl Glycinate

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of tert-Butyl Glycinate

* 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 [ 6456-74-2 ]

[ 6456-74-2 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 6456-74-2 ]
  • [ 17823-69-7 ]
  • [ 118534-48-8 ]
  • 2
  • [ 6456-74-2 ]
  • [ 132874-06-7 ]
  • [ 681430-73-9 ]
  • 3
  • [ 6456-74-2 ]
  • [ 37091-73-9 ]
  • 2-(tert-butyloxycarbonylmethylimino)-1,3-dimethylimidazolidine [ No CAS ]
  • 4
  • [ 6456-74-2 ]
  • [ 50595-15-8 ]
  • 5
  • [ 6456-74-2 ]
  • [ 42017-89-0 ]
  • [ 1094101-23-1 ]
YieldReaction ConditionsOperation in experiment
79% With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; Coupling of fenofbric acid (1) with EDC / HOBT in Dichloromethane followed by t-butylglycine gave t-butyl protected 118 in 79% yield after chromatography (ethyl acetate/hexane) 1H-NMR (CDCl3): delta 7.74 (d, 2H, J= 9 Hz), 7.72 (d, 2H, J= 9 Hz), 7.53 (d, 2H, J= 8 Hz), 7.10 (d, 2H, J= 8 Hz), 3.83 (s, 2H), 1.60 (s, 6H), 1.45 (s, 9H) ppm.
  • 6
  • [ 6456-74-2 ]
  • [ 68858-20-8 ]
  • [ 198561-07-8 ]
  • [ 1134204-67-3 ]
  • 7
  • [ 6456-74-2 ]
  • [ 21080-80-8 ]
  • [ 1263082-20-7 ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; at 130℃; for 4h; To a solution of a compound 1 (262 mg, 2.0 mmol) in toluene (5 mL) were added a compound II (368 mg, 2.0 mmol) and p-toluenesulfonic acid monohydrate (19 mg, 0.1 mmol), and the resulting solution was stirred at 130 °C for 4 hours. The reaction mixture was poured into saturated sodium bicarbonate aqueous solution and extracted with ethyl acetate, then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, concentrated in vacuo to give a compound III (281 mg, Yield 47percent) as yellow oil. The obtained compound III was used for the next reaction without further purification. 1 H NMR (DMSO-d6) delta: 0.78-0.84 (m, 4H), 1.24-1.28 (m, 3H), 1.40 (s, 9H), 1.90-2.00 (m, 1H), 4.10-4.25 (m ,4.H), 5.78 (d, J = 1.2 Hz, 1H), 10.01 (brs, 1H).
  • 8
  • [ 5683-31-8 ]
  • [ 6456-74-2 ]
  • tert-butyl 2-(3-(trimethylsilyl)propiolamido)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% Isobutyl chloroformate (357.2 mg, 2.6 mmol) was dropwise added to a solution of <strong>[5683-31-8]3-(trimethylsilyl)propiolic acid</strong> 25 (372 mg, 2.6 mmol) and NMM (344 mg, 3.4 mmol) in THF (10 mL) at -40 oC. The reaction was stirred at -40 to -10 oC for 40 min. A solution of tert-butyl 2-aminoacetate 26 (447 mg, 3.4 mmol) and NMM (344 mg, 3.4 mmol) in co-solvents THF/DMF (5 mL/1 mL) was slowly added to the reaction solution at -40 oC for 20 min. The mixture slowly recovered to r.t. from -40oC and was stirred overnight at r.t.. After concentration, the residue was dissolved in CH2Cl2, washed by NaHCO3 and brine, dried by Na2SO4 and purified by silica gel column chromatography (5-10% EtOAc/Hexanes, stepwise gradient by 5%, then 10% iPrOH /Hexanes) to afford 27. Yield: 428 mg, 64%. 1H NMR (CDCl3, 600 MHz) 6.41 (b, 1H), 3.97 (d, J = 5.4 Hz, 1H), 1.49 (s, 9H), 0.23 (s, 9H). MS (ESI) [M+H]+ 256.4, found 256.0.
  • 9
  • [ 201230-82-2 ]
  • [ 6456-74-2 ]
  • [ 131818-17-2 ]
  • [ 1597414-90-8 ]
  • 10
  • [ 6456-74-2 ]
  • [ 1641-69-6 ]
  • [ 131818-17-2 ]
  • [ 1622398-91-7 ]
  • 11
  • [ 6456-74-2 ]
  • [ 122889-11-6 ]
  • [ 675882-22-1 ]
YieldReaction ConditionsOperation in experiment
85% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; Amino acid S30 (27 mg, 0.065 mmol) and S31 (10 mg, 0.0599 mmol) were dissolved in 0.6 mL dry DMF, followed by addition of HATU (30mg, 0.077mmol), DIPEA (25|xL 0.1797 mmol). The resulting mixture was stirred under room temperature overnight and diluted with EtOAc. The solution was washed with 1M HCl and a saturated aqueous NaHCO3 solution. The combined organic phase was dried over Na2SO4 and concentrated, purified by silica gel column to afford compound S32 (27 mg, 85percent).
  • 12
  • [ 1122-12-9 ]
  • [ 6456-74-2 ]
  • (3,4-dibromo-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)acetic acid tert-butyl ester [ No CAS ]
  • 13
  • [ 2483-51-4 ]
  • [ 6456-74-2 ]
  • [ 35766-23-5 ]
YieldReaction ConditionsOperation in experiment
48% With 2,2':6',2'':6'',2'''-quaterpyridine; pentamethoxy tantalum; at 70℃; for 48h; Amide compounds were produced by reacting an aminoester compound with an amino compound under the respective reaction conditions below in the presence of a Ta(OMe)5 catalyst and a ligand. The yield for each product is indicated below the formula. In the reaction formula below, L-ala represents an L-alanine residue, Val represents an L-valine residue, Leu represents an L-Leucine residue, ILe represents an L-isoleucine residue, Gly represents glycine residue, Phe represents an L-phenylalanine residue, and Thr(OtBu) represents O-(tert butyl) L-threonine residue.
 

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