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

HRID 2230299Notes

Reaction equation

HRID 2230299 reaction equation
[N:1]1([C:8]([NH:10][C@@H:11](C)[C:12]([OH:14])=O)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:16]([O:20][C:21](=[O:39])[C@@H:22]([NH2:38])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)([CH3:19])([CH3:18])[CH3:17]>>[C:16]([O:20][C:21](=[O:39])[CH:22]([NH:38][C:12](=[O:14])[CH2:11][NH:10][C:8]([N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1)=[O:9])[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:26][CH:25]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

3

Reactant 2

HCID 11151579tert-butyl (2S)-2-amino-3-[4-(benzyloxy)phenyl]propanoateHCID 12968581(s)-2-[(Azepane-1-carbonyl)-amino]-propanoic acid

Product 1

HCID 700609632-{2-[(Azepane-1-carbonyl)-amino]-acetylamino}-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl esterYield 46.3%

Procedure

A solution of the product from Example AE ((S)-2-[(azepane-1-carbonyl)-amino]-propanoic acid) (0.50 g, 2.38 mmol) and the product from Example A ((S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.76 g, 2.33 mmol) were coupled according to the procedure described in Example AH. The reaction mixture was purified by chromatography (silica gel, 1:1 EtOAc/heptane) to give the title compound as a white foam (0.55 g, 43%).

Workup

  1. customThe reaction mixture was purified by chromatography (silica gel, 1:1 EtOAc/heptane)

Sources & evidence

ORD record
ord-fe13dfca69714aa8824eee71b86a7964
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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