Acetic Anhydride → HCID 70430585, compound

HRID 978341Notes

Reaction equation

HRID 978341 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([OH:16])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[C:26]([Cl:27])[C:11]=3[S:10]2)=[CH:5][CH:4]=1.[C:28](OC(=O)C)(=[O:30])[CH3:29]>N1C=CC=CC=1>[OH2:2].[ClH:27].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[C@@H:15]([O:16][C:28](=[O:30])[CH3:29])[C:14](=[O:17])[N:13]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[C:12]3[CH:23]=[CH:24][CH:25]=[C:26]([Cl:27])[C:11]=3[S:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 67941806HCID 67941806, compound

Product 1

HCID 70430585HCID 70430585, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 2.84 g of (+)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-9-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 30 ml of acetic anhydride and 30 drops of pyridine is stirred at 100° C. for 4 hours. After the reaction is completed, the reaction mixture is evaporated under reduced pressure to remove solvent. Toluene is added to the residue, and the mixture is evaporated under reduced pressure to remove solvent. The residue is converted to its hydrochloride and recrystallized from a mixture of ethanol and ether. 3.02 g of (+)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(dimethylamino)ethyl]-9-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride hydrate are obtained.

Workup

  1. customthe reaction mixture is evaporated under reduced pressure
  2. customto remove solvent
  3. additionToluene is added to the residue
  4. customthe mixture is evaporated under reduced pressure
  5. customto remove solvent
  6. customrecrystallized from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-99a3299b1e6548519ee63bf00270373e
Source dataset
uspto-grants-1987_05
Patent number
US04665068

Reaction notes

Loading…