Acetic Acid Mixture with Hydrobromic Acid → HCID 70493723, compound

HRID 1981946Notes

Reaction equation

HRID 1981946 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C:13](=[O:19])[N:12]([CH2:20][CH2:21][N:22](C(OCC3C=CC=CC=3)=O)[CH3:23])[C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]=3[S:9]2)=[CH:4][CH:3]=1.[BrH:38].C(O)(=O)C>C(O)(=O)C>[BrH:38].[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C:13](=[O:19])[N:12]([CH2:20][CH2:21][NH:22][CH3:23])[C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]=3[S:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 70493664HCID 70493664, compound

Product 1

HCID 70493723HCID 70493723, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.1 g of (±)-cis-2-(4-methylphenyl)-3-acetoxy-5-[2-(N-benzyloxycarbonyl-N-methylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one, 5 ml of acetic acid and 10 ml of 25% hydrogen bromide-acetic acid is stirred at room temperature for 2 hours. After the reaction is completed, the mixture is concentrated under reduced pressure. Toluene is added to the residue, and the mixture is evaporated to remove solvent. Crystalline precipitates are collected by filtration and washed with ether. Then, the crystals are recrystallized from isopropanol. 0.7 g of (±)-cis-2-(4-methylphenyl)-3-acetoxy-5-[2-(N-methylamino)ethyl]-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrobromide is obtained as prisms.

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. additionToluene is added to the residue
  3. customthe mixture is evaporated
  4. customto remove solvent
  5. customCrystalline precipitates
  6. filtrationare collected by filtration
  7. washwashed with ether
  8. customThen, the crystals are recrystallized from isopropanol

Sources & evidence

ORD record
ord-7f2f30bca0204380826210c78a5d9d0d
Source dataset
uspto-grants-1986_06
Patent number
US04594342

Reaction notes

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