L-Alanine → [(4-Nitrophenyl)methylcarbonyl]-L-alanine

HRID 1600135Notes

Reaction equation

HRID 1600135 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10]OC(=O)OC2C=CC([N+]([O-])=O)=CC=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:24][C@H:25]([C:27]([OH:29])=[O:28])[CH3:26].[CH2:30]([OH:32])C.O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:30]([NH:24][C@H:25]([C:27]([OH:29])=[O:28])[CH3:26])=[O:32])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 5950L-AlanineHCID 19096565Water ethanolHCID 21829967Carbonic acid 4-Nitrophenyl (4-Nitrophenyl)methyl Ester

Product 1

HCID 28215877[(4-Nitrophenyl)methylcarbonyl]-L-alanine

Procedure

The title compound is prepared by the procedure of Example 255 using 5.3 g of product from Example 254, 1.48 g of L-alanine, 4.6 ml of triethylamine,and 200 ml of 80/20 ethyl alcohol/water. The resulting oil is purified by chromatography (3X, silica gel: 50% ethyl acetate/hexane) to give 3.39 g of the desired product.

Workup

  1. customThe resulting oil is purified by chromatography (3X, silica gel: 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d8f0fae98fe04d6f86c445c1fe0c83e4
Source dataset
uspto-grants-1998_04
Patent number
US05744465

Reaction notes

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