Acetic Anhydride → HCID 86740803, compound

HRID 280515Notes

Reaction equation

HRID 280515 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]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:12]=3[S:11]2)=[CH:6][CH:5]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(O)(=O)C>[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:30](=[O:32])[CH3:31])[C:15](=[O:18])[N:14]([CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[C:13]3[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:12]=3[S:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 86740804HCID 86740804, compound

Product 1

HCID 86740803HCID 86740803, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1 g of (±)-cis-2-(4-methoxyphenyl)-3-hydroxy-5-[2-(dimethylamino)ethyl]-7-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride, 1.5 ml of acetic anhydride and 1.5 ml of acetic acid is stirred at 110° C. for 4 hours. After the reaction is completed, the mixture is evaporated under reduced pressure to remove acetic anhydride and acetic acid. Benzene is added to the residue, and the mixture is evaporated under reduced pressure to remove acetic anhydride and acetic acid. The residue thus obtained is recrystallized from a mixture of ethanol and ether. 0.87 g of (±)-cis-2-(4-methoxyphenyl)-3-acetoxy-5-[2-(dimethylamino)ethyl]-7-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride 1/2 hydrate is obtained. Yield: 78%

Workup

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

Sources & evidence

ORD record
ord-d63d8a8bd09243d1ae4a36045e09d10d
Source dataset
uspto-grants-1986_05
Patent number
US04590188

Reaction notes

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