Diethyl Ether → 3(R)-[1(R)-ethoxycarbonyl-4-(4-piperidyl)butyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid.dihydrobromide

HRID 980597Notes

Reaction equation

HRID 980597 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][C@@H:20]([NH:26][C@@H:27]2[C:33](=[O:34])[N:32]([CH2:35][C:36]([O:38]C(C)(C)C)=[O:37])[C:31]3[CH:43]=[CH:44][CH:45]=[CH:46][C:30]=3[S:29][CH2:28]2)[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.[BrH:47].C(O)(=O)C.C(OCC)C>C(O)(=O)C>[BrH:47].[BrH:47].[CH2:24]([O:23][C:21]([C@H:20]([NH:26][C@@H:27]1[C:33](=[O:34])[N:32]([CH2:35][C:36]([OH:38])=[O:37])[C:31]2[CH:43]=[CH:44][CH:45]=[CH:46][C:30]=2[S:29][CH2:28]1)[CH2:19][CH2:18][CH2:17][CH:14]1[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]1)=[O:22])[CH3:25]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 54047948tert-butyl 3(R)-[4-(1-benzyloxycarbonyl-4-piperidyl)-1(R)-ethoxycarbonylbutyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate

Product 1

HCID 704166013(R)-[1(R)-ethoxycarbonyl-4-(4-piperidyl)butyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid.dihydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 2 ml of acetic acid is dissolved 0.4 g of tert-butyl 3(R)-[4-(1-benzyloxycarbonyl-4-piperidyl)-1(R)-ethoxycarbonylbutyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate, and 2 ml of 30% hydrogen bromide-acetic acid solution is added to the solution, followed by allowing the mixture to stand at room temperature for 1.5 hours. Ethyl ether (50 ml) is added to the reaction solution, which is then allowed to stand. The supernatant is decanted, and the precipitate is washed with ethyl ether and dried to give 0.4 g of 3(R)-[1(R)-ethoxycarbonyl-4-(4-piperidyl)butyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid.dihydrobromide as a colorless powder.

Workup

  1. additionis added to the solution
  2. customThe supernatant is decanted
  3. washthe precipitate is washed with ethyl ether
  4. customdried

Sources & evidence

ORD record
ord-6aa69213ea384e46934e5878c2eb5ca8
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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