Acetic Anhydride → HCID 70430585, compound

HRID 978340Notes

Reaction equation

HRID 978340 reaction equation
O.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[C@@H:17]([OH:18])[C:16](=[O:19])[N:15]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:14]3[CH:25]=[CH:26][CH:27]=[C:28]([Cl:29])[C:13]=3[S:12]2)=[CH:7][CH:6]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(O)(=O)C>[OH2:4].[ClH:29].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[C@@H:17]([O:18][C:30](=[O:32])[CH3:31])[C:16](=[O:19])[N:15]([CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[C:14]3[CH:25]=[CH:26][CH:27]=[C:28]([Cl:29])[C:13]=3[S:12]2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 70461456HCID 70461456, compound

Product 1

HCID 70430585HCID 70430585, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 0.95 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-9-chloro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride hydrate, 10 ml of acetic anhydride and 10 ml of acetic acid is stirred at 110° C. for 6.5 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 recrystallized from a mixture of methanol and ether. 0.93 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 is obtained. Yield: 89.4%

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. customThe residue is recrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-751eecfd4df44982890d44364f2582fc
Source dataset
uspto-grants-1987_05
Patent number
US04665068

Reaction notes

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