Water → HCID 67916895, compound

HRID 654665Notes

Reaction equation

HRID 654665 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]CC3C=CC=CC=3)=[O:19])[C:14](=[O:28])[N:13]([CH2:29][CH2:30][N:31]([CH3:33])[CH3:32])[C:12]3[CH:34]=[CH:35][CH:36]=[CH:37][C:11]=3[S:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].O>C(O)C>[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:28])[N:13]([CH2:29][CH2:30][N:31]([CH3:32])[CH3:33])[C:12]3[CH:34]=[CH:35][CH:36]=[CH:37][C:11]=3[S:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70091379HCID 70091379, compound

Product 1

HCID 67916895HCID 67916895, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A mixture of a solution of (±)-cis-2-(4-methoxyphenyl)-3-(benzyloxycarbonylmethyl)oxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (880 mg) in a mixed solvent of 10% aqueous sodium hydroxide solution (2 ml), water (15 ml) and ethanol (15 ml) is stirred at 50° C. for 30 minutes. After the completion of the reaction, ethanol is distilled off under reduced pressure. The aqueous layer is washed with ethyl acetate and acidified with acetic acid under ice-cooling, and then, saturated with ammonium sulfate. The precipitated crystal is collected by filtration, washed with water and dried to give (±)-cis-2-(4-methoxyphenyl)-3-(carboxymethyl)oxy-5-[2-(dimethylamino)-ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (230 mg), m.p. 184°-188° C. (decomposed).

Workup

  1. distillationis distilled off under reduced pressure
  2. washThe aqueous layer is washed with ethyl acetate
  3. temperaturecooling
  4. filtrationThe precipitated crystal is collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-57fa5e6f07bd420094252acf2e6aa338
Source dataset
uspto-grants-1992_07
Patent number
US05134139

Reaction notes

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