HCID 70416343, compound → HCID 53869746, compound

HRID 1284948Notes

Reaction equation

HRID 1284948 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>C(O)C.[OH-].[Na+].O>[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 1

HCID 70416343HCID 70416343, compound

Product 1

HCID 53869746HCID 53869746, compoundYield 85.8%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 3(R)-(5-benzyloxycarbonylamino-1-ethoxycarbonylpentyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetate hydrochloride (55 mg) obtained in Example 52-(1) is dissolved in a mixture of ethanol (3 ml) and 1N aqueous sodium hydroxide (2 ml). The solution is allowed to stand for 1 hour at room temperature, diluted with water (50 ml) and extracted with ethyl ether (20 ml). The aqueous layer is acidified to pH 4 with 1N hydrochloric acid, saturated with ammonium chloride and extracted ten times with ethyl acetate (20 ml each). The extract is washed with a small amount of water, dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure to yield 3(R)-(5-benzyloxycarbonylamino-1-carboxypentyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzothiazepine-5-acetic acid (40 mg) as colorless powder.

Workup

  1. extractionextracted with ethyl ether (20 ml)
  2. extractionextracted ten times with ethyl acetate (20 ml each)
  3. washThe extract is washed with a small amount of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-2fb2b5dbc2ee4c41802b1d0ea0d5112c
Source dataset
uspto-grants-1986_01
Patent number
US04564612

Reaction notes

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