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

HRID 1290420Notes

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].C(N(CC)CC)C.[CH2:37]([OH:39])C.O>>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:37]([NH:24][C@H:25]([C:27]([OH:29])=[O:28])[CH3:26])=[O:39])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Reactant 4

HCID 5950L-Alanine

HCID 8471Triethylamine

HCID 19096565Water ethanol

HCID 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 (3×, silica gel: 50% ethyl acetate/hexane) to give 3.39 g of the desired product.

Workup

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

Sources & evidence

ORD record: ord-ca9fb0497eea4da3b7ce11ef4fe617f2
Source dataset: uspto-grants-1998_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05750735

Reaction notes

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