Ethyl 4-nitro-3-phenyl-L-alaninate monohydrochloride → ethyl (S)-2-[(N-benzyloxycarbonyl-4-piperidinyloxy)acetylamino]-3-(4-nitrophenyl)propionate

HRID 1682678Notes

Reaction equation

HRID 1682678 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][CH2:18][C:19]([OH:21])=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:23][C@@H:24]([CH2:30][C:31]1[CH:36]=[CH:35][C:34]([N+:37]([O-:39])=[O:38])=[CH:33][CH:32]=1)[C:25]([O:27][CH2:28][CH3:29])=[O:26]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([O:17][CH2:18][C:19]([NH:23][C@@H:24]([CH2:30][C:31]2[CH:32]=[CH:33][C:34]([N+:37]([O-:39])=[O:38])=[CH:35][CH:36]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:21])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 6453710Ethyl 4-nitro-3-phenyl-L-alaninate monohydrochlorideHCID 189194942-((1-((Benzyloxy)carbonyl)piperidin-4-YL)oxy)acetic acid

Product 1

HCID 86750902ethyl (S)-2-[(N-benzyloxycarbonyl-4-piperidinyloxy)acetylamino]-3-(4-nitrophenyl)propionateYield 76.1%

Procedure

In the same manner as in Example 67 (1), [N-benzyloxycarbonyl-4-piperidinyloxy]acetic acid (530 mg, 1.81 mmol) and ethyl (S)-2-amino-3-(4-nitrophenyl)propionate hydrochloride (500 mg, 1.82 mmol) were condensed to give 707 mg of ethyl (S)-2-[(N-benzyloxycarbonyl-4-piperidinyloxy)acetylamino]-3-(4-nitrophenyl)propionate as a yellow oil (76%).

Workup

  1. customcondensed

Sources & evidence

ORD record
ord-79391802f8694f27ad034bf1e60ed4f2
Source dataset
uspto-grants-1997_06
Patent number
US05635527

Reaction notes

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