Acetic Acid → HCID 13652683, compound

HRID 980591Notes

Reaction equation

HRID 980591 reaction equation
Br.Br.C([O:5][C:6]([C@@H:8]([NH:17][C@@H:18]1[C:24](=[O:25])[N:23]([CH2:26][C:27]([OH:29])=[O:28])[C:22]2[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=2[S:20][CH2:19]1)[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:7])C.C(O)(=O)C>[OH-].[Na+]>[C:6]([C@@H:8]([NH:17][C@@H:18]1[C:24](=[O:25])[N:23]([CH2:26][C:27]([OH:29])=[O:28])[C:22]2[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=2[S:20][CH2:19]1)[CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 70416573HCID 70416573, compound

Product 1

HCID 13652683HCID 13652683, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 4 ml of 0.1N aqueous sodium hydroxide solution is dissolved 0.15 g of 3(R)-[1(S)-ethoxycarbonyl-3-(4-piperidyl)propyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid.dihydrobromide as obtained in Example 72, and the solution is allowed to stand at room temperature for 2 hours. The solution is made weakly acidified with 1 ml of acetic acid, and purified by Amberlite XAD-2 column chromatography (methanol:water=1:1). The eluate is concentrated under reduced pressure, and the residue is lyophilized to give 0.06 g of 3(R)-[1(S)-carboxy-3-(4-piperidyl)propyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid as a colorless powder.

Workup

  1. customas obtained in Example 72
  2. custompurified by Amberlite XAD-2 column chromatography (methanol:water=1:1)
  3. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-d452365612a741bcb686cd45d2079f92
Source dataset
uspto-grants-1987_01
Patent number
US04638000

Reaction notes

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