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

HRID 2230297Notes

Reaction equation

HRID 2230297 reaction equation
[N:1]1([C:8]([NH:10][C@@H:11]([CH:15]([CH3:18])[CH2:16][CH3:17])[C:12]([OH:14])=O)=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([O:23][C:24](=[O:42])[C@@H:25]([NH2:41])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:29][CH:28]=1)([CH3:22])([CH3:21])[CH3:20]>>[C:19]([O:23][C:24](=[O:42])[C@@H:25]([NH:41][C:12](=[O:14])[C@@H: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]([CH3:18])[CH2:16][CH3:17])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:29][CH:28]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

3

Reactant 2

HCID 11151579tert-butyl (2S)-2-amino-3-[4-(benzyloxy)phenyl]propanoateHCID 12968579HCID 12968579, compound

Product 1

HCID 12968569(S)-2-{(S)-2-[(Azepane-1-carbonyl)-amino]-3-methyl-pentanoylamino}-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester

Procedure

A solution of the product from Example AB ((S)-2-[(azepane-1-carbonyl)-amino]-3-methyl-pentanoic acid) (0.50 g, 1.95 mmol) and the product from Example A ((S)-2-amino-3-(4-benzyloxy-phenyl)-propionic acid tert-butyl ester) (0.63 g, 1.95 mmol) were coupled according to the procedure described in Example AH. The crude reaction product was purified by chromatography (silica gel, 1:1 EtOAc/heptane) to give the title compound as a white foam, mp=53-57° C.

Workup

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

Sources & evidence

ORD record
ord-e0d6376f985d425f94f9bfd79931920d
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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