N-(tert-butoxycarbonyl)glycine → N-t-Butoxycarbonylglycyl-3(R)-methyl-beta-alanine benzyl ester

HRID 618162Notes

Reaction equation

HRID 618162 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([O:20][C:21](=[O:26])[CH2:22][C@@H:23]([CH3:25])[NH2:24])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCCCCC.CCOC(C)=O>[CH2:13]([O:20][C:21](=[O:26])[CH2:22][C@@H:23]([CH3:25])[NH:24][C:10](=[O:12])[CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 10867189(R)-Benzyl 3-aminobutyrate

Product 1

HCID 86751222N-t-Butoxycarbonylglycyl-3(R)-methyl-beta-alanine benzyl ester

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

N-(t-Butoxycarbonyl)glycine 14-3 (Aldrich) was coupled with 3(R)-methyl-β-alanine benzyl ester 0.5 H2SO4 11-7 (Celgene) according to the procedure described for the preparation of 14-5. The title product 15-1 was then obtained by chromatography (silica, hexane/EtOAc 2:3).

Workup

  1. customdescribed for the preparation of 14-5

Sources & evidence

ORD record
ord-f686645fd6fb444f9a02da3ec36d6243
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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