Sodium Hydroxide → HCID 70456300, compound

HRID 1284943Notes

Reaction equation

HRID 1284943 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:20]2[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=2[S:18][CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].ClC1C=CC=C(C(OO)=[O:44])C=1.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C@@H:6]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C:20]2[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=2[S:18](=[O:44])[CH2:17]1)[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acid2×HCID 13454547HCID 13454547, compound

Product 1

HCID 70456300HCID 70456300, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 g of tert-butyl 3(R)-[1(S)-ethoxycarbonyl-3-phenylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate obtained in Example 1 in 100 ml of methylene chloride is added 0.51 g of m-chloroperbenzoic acid. After stirring for 30 minutes, 0.15 g of m-chloroperbenzoic acid is added, and stirring is continued for further 30 minutes. Fifty ml of 1N aqueous sodium hydroxide is added to the mixture, and the methylene chloride layer is separated, washed with water and concentrated under reduced pressure to yield tert-butyl 3(R)-[1(S)-ethoxycarbonyl-3-phenylpropyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate 1-oxide as a mixture of two stereoisomers. Separation by silica gel column chromatography yields 0.3 g of one isomer and 0.5 g of another isomer. Both are obtained as colorless oil. Mass spectrum of each isomer shows the peak due to molecular ion at 514.

Workup

  1. stirringstirring
  2. waitis continued for further 30 minutes
  3. customthe methylene chloride layer is separated
  4. washwashed with water
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6e7074bded4d4793b4c85c02a3fe8b93
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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