Sodium hydride → tert-butyl 4-oxo-3(R)-phthalimido-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate
Reaction equation
[H-].[Na+].[C:3]1(=[O:25])[N:7]([C@@H:8]2[C:14](=[O:15])[NH:13][C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[S:10][CH2:9]2)[C:6](=[O:20])[C:5]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:4]12.Cl[CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CN(C)C=O>[O:15]=[C:14]1[N:13]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[S:10][CH2:9][C@@H:8]1[N:7]1[C:6](=[O:20])[C:5]2=[CH:21][CH:22]=[CH:23][CH:24]=[C:4]2[C:3]1=[O:25]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred mixture of 50 ml of N,N-dimethylformamide and 0.5 g of sodium hydride (60% in oil) is added 4 g of 3(R)-phthalimido-2,3-dihydro-1,5(5H)-benzothiazepin-4-one obtained in Reference Example 2 at ice bath temperature. After 5 minutes, 2 g of tert-butyl chloroacetate is added at ice bath temperature. The resulting mixture is stirred in an ice bath for b 15 minutes and diluted with ice water (200 ml). The deposited crystals are collected by filtration, dried and purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give 4 g of tert-butyl 4-oxo-3(R)-phthalimido-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate as colorless crystals. Recrystallization of a part of the crystals from ethyl ether yields colorless prisms, m.p. 181°-184° C.
Workup
- customobtained in Reference Example 2 at ice bath temperature
- filtrationThe deposited crystals are collected by filtration
- customdried
- custompurified by silica gel column chromatography (hexane:ethyl acetate=3:1)
Sources & evidence
- ORD record
- ord-8ea5cc954a324c1b839d8207c707cf35
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04564612
Reaction notes
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