Acetic Acid Mixture with Hydrobromic Acid → HCID 22837852, compound

HRID 980589Notes

Reaction equation

HRID 980589 reaction equation
C(OC([NH:11][C@@H:12]1[C:18](=[O:19])[N:17]([CH2:20][C:21]([O:23]C(C)(C)C)=[O:22])[C:16]2[CH:28]=[C:29]([C:32]([F:35])([F:34])[F:33])[CH:30]=[CH:31][C:15]=2[S:14][CH2:13]1)=O)C1C=CC=CC=1.[BrH:36].C(O)(=O)C>C(O)(=O)C>[BrH:36].[NH2:11][C@@H:12]1[C:18](=[O:19])[N:17]([CH2:20][C:21]([OH:23])=[O:22])[C:16]2[CH:28]=[C:29]([C:32]([F:35])([F:34])[F:33])[CH:30]=[CH:31][C:15]=2[S:14][CH2:13]1

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 54033484HCID 54033484, compound

Product 1

HCID 22837852HCID 22837852, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 5 ml of acetic acid is dissolved 1.4 g of tert-butyl 3(R)-benzyloxycarbonylamino-4-oxo-7-trifluoromethyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, and 10 ml of 30% hydrogen bromide-acetic acid solution is added to the solution, followed by allowing the mixture to stand at room temperature for 4 hours. Petroleum ether (100 ml) is added to the reaction solution, and the mixture is thoroughly shaken, followed by decanting the supernatant. After petroleum ether is again added to repeat the same procedure, the residue is dissolved in a mixture of ethyl acetate and benzene, and the mixture is concentrated to dryness under reduced pressure. Petroleum ether is added to the residue to give 0.75 g of 3(R)-amino-4-oxo-7-trifluoromethyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid hydrobromide as crystals.

Workup

  1. additionis added to the solution
  2. customby decanting the supernatant
  3. additionAfter petroleum ether is again added
  4. dissolutionthe residue is dissolved in a mixture of ethyl acetate and benzene
  5. concentrationthe mixture is concentrated to dryness under reduced pressure
  6. additionPetroleum ether is added to the residue

Sources & evidence

ORD record
ord-f3274c31e4564ad9b89423ba351622f1
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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