Water → HCID 53869746, compound

HRID 649378Notes

Reaction equation

HRID 649378 reaction equation
Cl.[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([NH:23][C@@H:24]1[C:30](=[O:31])[N:29]([CH2:32][C:33]([O:35]CC)=[O:34])[C:28]2[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=2[S:26][CH2:25]1)[C:18]([O:20]CC)=[O:19])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O>C(O)C.[OH-].[Na+]>[CH2:2]([O:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([NH:23][C@@H:24]1[C:30](=[O:31])[N:29]([CH2:32][C:33]([OH:35])=[O:34])[C:28]2[CH:38]=[CH:39][CH:40]=[CH:41][C:27]=2[S:26][CH2:25]1)[C:18]([OH:20])=[O:19])=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 962WaterHCID 70416343HCID 70416343, compound

Product 1

HCID 53869746HCID 53869746, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

In a mixture of 3 ml of ethanol and 2 ml of 1N aqueous sodium hydroxide solution is dissolved 55 mg of ethyl 3(R)-(5-benzyloxycarbonylamino-1-ethoxycarbonylpentyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate.hydrochloride as obtained in Example 50, and the solution is allowed to stand at room temperature for 1 hour. Water(50 ml) is added to the reaction solution, and after the mixture is extracted with 20 ml of ethyl ether, the aqueous layer is adjusted to pH 4 with 1N hydrochloric acid. Ammonium chloride is added to the solution until it becomes saturated, and the aqueous layer is extracted ten times with 20 ml of ethyl acetate. The extract is washed with a small amount of water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 40 mg of 3(R)-(5-benzyloxycarbonylamino-1-carboxypentyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid as a colorless powder.

Workup

  1. customas obtained in Example 50
  2. extractionafter the mixture is extracted with 20 ml of ethyl ether
  3. additionAmmonium chloride is added to the solution until it
  4. extractionthe aqueous layer is extracted ten times with 20 ml of ethyl acetate
  5. washThe extract is washed with a small amount of water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-696ef7071f09487588fd9e7a235f1ccb
Source dataset
uspto-grants-1988_04
Patent number
US04739066

Reaction notes

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