Acetic Acid → HCID 54358185, compound

HRID 464867Notes

Reaction equation

HRID 464867 reaction equation
Cl.Cl.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[O: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+].O.CO>[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[O: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

5

Reactant 2

HCID 176Acetic AcidHCID 70045191HCID 70045191, compound

Product 1

HCID 54358185HCID 54358185, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

A solution of 3(S)-[1(S)-ethoxycarbonyl-4-(4-piperidyl)butyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid dihydrochloride (0.35 g) in 1N sodium hydroxide solution (8 ml) is allowed to stand for 30 minutes at room temperature. After addition of acetic acid (1.5 ml), the mixture is subjected to column chromatography on MCI gel (CHP 20P, 150-300μ, Mitsubishi Chemical) using water-methanol (2:1) as an eluent. The eluate is concentrated in vacuo and lyophilized to yield 3(S)-[1(S)-carboxy-4-(4-piperidyl)butyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid (0.2 g) as colorless powder.

Workup

  1. concentrationThe eluate is concentrated in vacuo

Sources & evidence

ORD record
ord-85b1b65b2ad34e78a8fb2fe6dbad0844
Source dataset
uspto-grants-1985_10
Patent number
US04548932

Reaction notes

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