Acetic Acid → HCID 70069849, compound

HRID 1638993Notes

Reaction equation

HRID 1638993 reaction equation
C([O:3][C:4]([C@@H:6]([NH:17][CH:18]1[CH2:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]([CH2:29][C:30]([O:32]CC)=[O:31])[C:19]1=[O:35])[CH2:7][S:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)=[O:5])C.[OH-].[Na+].C(O)(=O)C>CO>[OH2:3].[C:4]([C@@H:6]([NH:17][CH:18]1[CH2:24][CH2:23][C:22]2[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=2[N:20]([CH2:29][C:30]([OH:32])=[O:31])[C:19]1=[O:35])[CH2:7][S:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 14675937HCID 14675937, compound

Product 1

HCID 70069849HCID 70069849, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.3 g of dihydrobromide of the B-isomer of ethyl 3-[1(R)-ethoxycarbonyl-2-{2-(4-piperidyl)ethylthio}ethyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetate obtained in Example 5 is dissolved in 10 ml of an aqueous solution of 50% methanol, and the resulting solution is gradually added dropwise to 15.5 ml of an aqueous solution of 2N sodium hydroxide. After stirring for 2 hours at room temperature, the reaction liquid is neutralized with 6.5 ml of acetic acid. The residue obtained by concentration under reduced pressure is purified by HP-20 column chromatography (water:methanol=3:1). The solvent is evaporated under reduced pressure, and the resulting residue is lyophilized to give 440 mg of the B-isomer of 3-[1(R)-carboxy-2-{2-(4-piperidyl)ethylthio}ethyl]amino-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-1-acetic acid monohydrate as a colorless powder.

Workup

  1. customthe reaction liquid
  2. customThe residue obtained by concentration under reduced pressure
  3. customis purified by HP-20 column chromatography (water:methanol=3:1)
  4. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-b93cc19eb1a04255a992af8801d02077
Source dataset
uspto-grants-1989_11
Patent number
US04882326

Reaction notes

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