Acetic Acid → HCID 13652707, compound

HRID 649387Notes

Reaction equation

HRID 649387 reaction equation
Br.Br.C([O:5][C:6]([C@@H:8]([NH:18][C@@H:19]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([OH:30])=[O:29])[C:23]2[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=2[S:21][CH2:20]1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:7])C.C(O)(=O)C>[OH-].[Na+]>[C:6]([C@@H:8]([NH:18][C@@H:19]1[C:25](=[O:26])[N:24]([CH2:27][C:28]([OH:30])=[O:29])[C:23]2[CH:31]=[CH:32][CH:33]=[CH:34][C:22]=2[S:21][CH2:20]1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)([OH:7])=[O:5]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 70416348HCID 70416348, compound

Product 1

HCID 13652707HCID 13652707, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 12 ml of 1N aqueous sodium hydroxide solution is dissolved 0.5 g of 3(R)-[1(S)-ethoxycarbonyl-4-(4-piperidyl)butyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid.dihydrobromide, and the solution is allowed to stand at room temperature for 30 minutes. The solution is neutralized with 2 ml of acetic acid, and purified by MCI-gel (CHP 20P, 150 to 300μ, Mitsubishi Chemical Industries, Japan) column chormatography (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-4-(4-piperidyl)butyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid as a colorless powder.

Workup

  1. custompurified by MCI-gel (CHP 20P, 150 to 300μ, Mitsubishi Chemical Industries, Japan) column chormatography (water:methanol=2:1)
  2. concentrationThe eluent is concentrated under reduced pressure

Sources & evidence

ORD record
ord-34d41b4901b34dc9a42c5d89d0df3034
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

Loading…