Potassium Hydroxide → HCID 10791242, compound

HRID 1981939Notes

Reaction equation

HRID 1981939 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:14]([OH:15])[C:13](=[O:16])[NH:12][C:11]3[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:10]=3[S:9]2)=[CH:4][CH:3]=1.[CH2:22]([O:29][C:30]([N:32]([CH2:34][CH2:35]Cl)[CH3:33])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH-].[K+]>CS(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:14]([OH:15])[C:13](=[O:16])[N:12]([CH2:35][CH2:34][N:32]([C:30]([O:29][CH2:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:31])[CH3:33])[C:11]3[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:10]=3[S:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 13592063Benzyl (2-chloroethyl)methylcarbamateHCID 67790739HCID 67790739, compound

Product 1

HCID 10791242HCID 10791242, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 5.96 g of (±)-cis-2-(4-methylphenyl)-3-hydroxy-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 5.89 g of 2-(N-benzyloxycarbonyl-N-methylamino)ethyl chloride, 1.68 g of potassium hydroxide and 85 ml of dimethylsulfoxide is treated in the same manner as described in Example 1-(1). The crude product thus obtained is purified by silica gel chromatography (solvent, benzene:ethyl acetate=9:1). 7.89 g of (±)-cis-2-(4-methylphenyl)-3-hydroxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-8-methyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one are obtained as an oil.

Workup

  1. additionis treated in the same manner
  2. customThe crude product thus obtained
  3. customis purified by silica gel chromatography (solvent, benzene:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-a7a936059f994c8b9c314ec4a834caf2
Source dataset
uspto-grants-1986_06
Patent number
US04594342

Reaction notes

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