Water → HCID 70124261, compound

HRID 654663Notes

Reaction equation

HRID 654663 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][CH2:17][C:18]([O:20]CC)=[O:19])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][N:26]([CH3:37])[CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)[C:12]3[CH:38]=[CH:39][CH:40]=[CH:41][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].O>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[C@@H:15]([O:16][CH2:17][C:18]([OH:20])=[O:19])[C:14](=[O:23])[N:13]([CH2:24][CH2:25][N:26]([CH3:37])[CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[C:12]3[CH:38]=[CH:39][CH:40]=[CH:41][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70090902HCID 70090902, compound

Product 1

HCID 70124261HCID 70124261, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (+)-cis-2-(4-methoxyphenyl)-3-(ethoxycarbonylmethyl)oxy-5-{2-[N-methyl-N-(4-methoxyphenethyl)amino]ethyl}-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (5.4 g), sodium hydroxide (423 mg), water (50 ml) and methanol (50 ml) is stirred at room temperature overnight. The reaction mixture is concentrated under reduced pressure, and water is added to the resulting residue. The mixture is washed with ether, and the pH value thereof is adjusted to 4 with 10% hydrochloric acid, and then extracted with a mixture of chloroform and isopropyl alcohol. The extract is washed, dried, and the solvent is distilled off to give (+)-cis- 2-(4-methoxyphenyl)-3-(carboxymethyl)oxy-5-{2-[N-methyl-N-(4-methoxyphenethyl)amino]ethyl}-2,3-dihydro-1,5-benzothiazepin-4-(5H)-one (4.57 g) as oily product.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, and water
  2. additionis added to the resulting residue
  3. washThe mixture is washed with ether
  4. extractionextracted with a mixture of chloroform and isopropyl alcohol
  5. washThe extract is washed
  6. customdried
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-2c6c0a4e4d7347d3913c0515e3310636
Source dataset
uspto-grants-1992_07
Patent number
US05134139

Reaction notes

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