Acetic Acid → CV 5975

HRID 980600Notes

Reaction equation

HRID 980600 reaction equation
Br.Br.C([O:5][C:6]([C@@H:8]([NH:19][C@@H:20]1[C:26](=[O:27])[N:25]([CH2:28][C:29]([OH:31])=[O:30])[C:24]2[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=2[S:22][CH2:21]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:7])C.C(O)(=O)C>[Na]>[C:6]([C@@H:8]([NH:19][C@@H:20]1[C:26](=[O:27])[N:25]([CH2:28][C:29]([OH:31])=[O:30])[C:24]2[CH:32]=[CH:33][CH:34]=[CH:35][C:23]=2[S:22][CH2:21]1)[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 136527133(R)-[1(S)-ethoxycarbonyl-5-(4-piperidyl)pentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid.dihydrobromide

Product 1

HCID 3035825CV 5975Yield 94.8%

Reagents, catalysts & solvents 1

HCID 5360545SodiumSolvent

Procedure

In 10 ml of 1N aqueous sodium hdyroxide solution is dissolved 0.45 g of 3(R)-[1(S)-ethoxycarbonyl-5-(4-piperidyl)pentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5acetic acid.dihydrobromide, and the solution is allowed to stand at room temperature for 30 minutes. The reaction solution is neutralized with 2 ml of acetic acid and purified by MCI gel column chromatography (water:methanol=2:1). The eluent is concentrated under reduced pressure and the residue is lyophilized to give 0.3 g of 3(R)-[1(S)-carboxy-5-(4-piperidyl)pentyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid as a colorless powder.

Workup

  1. custompurified by MCI gel column chromatography (water:methanol=2:1)
  2. concentrationThe eluent is concentrated under reduced pressure

Sources & evidence

ORD record
ord-34ff72b5571d4f15b0092724bfa45d9b
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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