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

HRID 464841Notes

Reaction equation

HRID 464841 reaction equation
[NH2:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[O:4][CH2:3]1.[CH:22]1([CH2:28][CH2:29][C:30](=O)[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH2:34]([O:33][C:31]([C@H:30]([NH:1][C@@H:2]1[C:8](=[O:9])[N:7]([CH2:10][C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[C:6]2[CH:18]=[CH:19][CH:20]=[CH:21][C:5]=2[O:4][CH2:3]1)[CH2:29][CH2:28][CH:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1)=[O:32])[CH3:35]

Participants

3

Reactant 2

HCID 13454680Ethyl 4-cyclohexyl-2-oxobutanoateHCID 13622530tert-butyl 3(S)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate

Product 1

HCID 70047571tert-butyl 3(S)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate

Procedure

Reaction of 9.5 g of tert-butyl 3(S)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate obtained in Example 26 and ethyl 4-cyclohexyl-2-oxobutyrate is carried out under reductive conditions in a manner similar to that described in Example 16, and the product is purified by silica gel column chromatography (hexane:ethyl acetate=5:1). From the first fraction, 2.3 g of tert-butyl 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. customthe product is purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-4a739653ee964005adfab89dc2b89680
Source dataset
uspto-grants-1985_10
Patent number
US04548932

Reaction notes

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