tert-butyl 3(R)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate → HCID 70456987, compound

HRID 1284939Notes

Reaction equation

HRID 1284939 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[S: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[S: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 13454543tert-butyl 3(R)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetateHCID 13454680Ethyl 4-cyclohexyl-2-oxobutanoate

Product 1

HCID 70456987HCID 70456987, compoundYield 12.2%

Procedure

In a manner similar to that described in Example 1, the reaction of 1.5 g of tert-butyl 3(R)-amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate with 5 g of ethyl 4-cyclohexyl-2-oxobutyrate obtained in Reference Example 5 is carried out, and the product is purified by silica gel column chromatography (hexane:ethyl acetate=4:1). From the first fraction is obtained 0.3 g of tert-butyl 3(R)-[1(R)-ethoxycarbonyl-3-cyclohexylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate as a colorless oil.

Workup

  1. customobtained in Reference Example 5
  2. customthe product is purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-2b514b8538474d06ab2da18073d42d73
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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