Acetic Anhydride → HCID 86740808, compound

HRID 280523Notes

Reaction equation

HRID 280523 reaction equation
[ClH:1].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C@H:10]2[C@@H:16]([OH:17])[C:15](=[O:18])[N:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:13]3[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:12]=3[S:11]2)=[CH:6][CH:5]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>>[ClH:1].[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([C@H:10]2[C@@H:16]([O:17][C:29](=[O:31])[CH3:30])[C:15](=[O:18])[N:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:13]3[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:12]=3[S:11]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 70482384HCID 70482384, compound

Product 1

HCID 86740808HCID 86740808, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 0.7 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-8-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride and 8 ml of acetic anhydride is heated at 100° C. for 4 hours. After the reaction is completed, the mixture is evaporated under reduced pressure to remove acetic anhydride and acetic acid. Toluene is added to the residue, and the mixture is evaporated under reduced pressure to remove solvent. The residue is recrystallized from a mixture of ethanol and ether. 0.68 g of (±)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(dimethylamino)ethyl]-8-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride 1/3H2O is obtained.

Workup

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

Sources & evidence

ORD record
ord-5509501603ac4d4d9aed495dbfdce287
Source dataset
uspto-grants-1986_05
Patent number
US04590188

Reaction notes

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