HCID 70416287, compound → HCID 53643713, compound

HRID 649382Notes

Reaction equation

HRID 649382 reaction equation
Cl.Cl.C([O:5][C:6]([CH:8]([NH:19][C@@H:20]1[C:26](=[O:27])[N:25]([CH2:28][C:29]([O:31]CC)=[O:30])[C:24]2[CH:34]=[CH:35][CH:36]=[CH:37][C:23]=2[S:22][CH2:21]1)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:7])C>CO.[OH-].[Na+]>[C:6]([CH: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:34]=[CH:35][CH:36]=[CH:37][C:23]=2[S:22][CH2:21]1)[CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)([OH:7])=[O:5]

Participants

4

Reactant 1

HCID 70416287HCID 70416287, compound

Product 1

HCID 53643713HCID 53643713, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

In a mixture of 1 ml of methanol and 1 ml of 1N aqueous sodium hydroxide solution is dissolved 30 mg of ethyl 3(R)-(1-ethoxycarbonyl-5-piperidinopentyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate.dihydrochloride as obtained in Example 79, and the solution is allowed to stand at room temperature for 1 hour. After methanol is evaporated off under reduced pressure, 2 ml of water and 0.5 ml of acetic acid are added to the residue, followed by purification by Amberlite XAD-2 column chromatography (acetone:water=2:1). The eluate is concentrated under reduced pressure, and the residue is lyophilized to give 17 mg of 3(R)-(1-carboxy-5-piperidinopentyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid as a colorless powder.

Workup

  1. customas obtained in Example 79
  2. customAfter methanol is evaporated off under reduced pressure, 2 ml of water and 0.5 ml of acetic acid
  3. additionare added to the residue
  4. customfollowed by purification by Amberlite XAD-2 column chromatography (acetone:water=2:1)
  5. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c1a8bf190bc14c53b6cc19ce58807d6b
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

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