Ethyl 4-cyclohexyl-2-oxobutanoate → benzyl 3(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate

HRID 464836Notes

Reaction equation

HRID 464836 reaction equation
Cl.[NH2:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[O:5][CH2:4]1.[CH:26]1([CH2:32][CH2:33][C:34](=O)[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>>[CH2:38]([O:37][C:35]([C@H:34]([NH:2][C@@H:3]1[C:9](=[O:10])[N:8]([CH2:11][C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[C:7]2[CH:22]=[CH:23][CH:24]=[CH:25][C:6]=2[O:5][CH2:4]1)[CH2:33][CH2:32][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]1)=[O:36])[CH3:39]

Participants

3

Reactant 2

HCID 13454680Ethyl 4-cyclohexyl-2-oxobutanoateHCID 18599732benzyl 3(S)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate hydrochloride

Product 1

HCID 70046892benzyl 3(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetateYield 18.5%

Procedure

Benzyl 3(S)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate hydrochloride (1.5 g) and ethyl 4-cyclohexyl-2-oxobutyrate (2.63 g) are subjected to reductive alkylation reaction in a manner similar to that described in Example 16, and the product is purified by silica gel column chromatography (hexane:ethal acetate=5:1-4:1). From the first fraction, 0.4 g of benzyl 3(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate is obtained as a colorless oil.

Workup

  1. customalkylation reaction in a manner similar to
  2. customthe product is purified by silica gel column chromatography (hexane:ethal acetate=5:1-4:1)

Sources & evidence

ORD record
ord-e588394232fc485292af739d6142339c
Source dataset
uspto-grants-1985_10
Patent number
US04548932

Reaction notes

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