tert-butyl (2S)-2-amino-3-[4-(benzyloxy)phenyl]propanoate → 2-{2-[(Azepane-1-carbonyl)-amino]-3-methyl-butyrylamino}-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

HRID 2230298Notes

Reaction equation

HRID 2230298 reaction equation
[N:1]1([C:8]([NH:10][C@@H:11]([CH:15]([CH3:17])[CH3:16])[C:12]([OH:14])=O)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18]([O:22][C:23](=[O:41])[C@@H:24]([NH2:40])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:28][CH:27]=1)([CH3:21])([CH3:20])[CH3:19]>>[C:18]([O:22][C:23](=[O:41])[CH:24]([NH:40][C:12](=[O:14])[CH:11]([NH:10][C:8]([N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:9])[CH:15]([CH3:17])[CH3:16])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:28][CH:27]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

3

Reactant 2

HCID 11151579tert-butyl (2S)-2-amino-3-[4-(benzyloxy)phenyl]propanoateHCID 12968580(s)-2-[(Azepane-1-carbonyl)-amino]-3-methyl-butanoic acid

Product 1

HCID 700591002-{2-[(Azepane-1-carbonyl)-amino]-3-methyl-butyrylamino}-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl esterYield 48.2%

Procedure

A solution of the product from Example AC ((S)-2-[(azepane-1-carbonyl)-amino]-3-methyl-butanoic acid) (0.50 g, 2.07 mmol) and the product from Example A ((S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.67 g, 2.07 mmol) were coupled according to the procedure described in Example AH. The crude reaction product was purified by chromatography (silica gel, EtOAc) to give the title compound as a white foam (0.55 g, 48%).

Workup

  1. customThe crude reaction product
  2. customwas purified by chromatography (silica gel, EtOAc)

Sources & evidence

ORD record
ord-63356514b1d9420aa0e377ab74737d7a
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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