Acetic Acid → HCID 13622630, compound

HRID 464861Notes

Reaction equation

HRID 464861 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:17][C@@H:18]1[C:24](=[O:25])[N:23]([CH2:26][C:27]([OH:29])=[O:28])[C:22]2[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=2[O:20][CH2:19]1)[C:12]([O:14]CC)=[O:13].C(O)(=O)C>[OH-].[Na+]>[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C@H:11]([NH:17][C@@H:18]1[C:24](=[O:25])[N:23]([CH2:26][C:27]([OH:29])=[O:28])[C:22]2[CH:30]=[CH:31][CH:32]=[CH:33][C:21]=2[O:20][CH2:19]1)[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13622612HCID 13622612, compound

Product 1

HCID 13622630HCID 13622630, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3(S)-[8-amino-1(S)-ethoxycarbonyloctyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid.dihydrochloride (0.3 g) in 1N sodium hydroxide solution (10 ml) is allowed to stand for 30 minutes at room temperature. After addition of acetic acid (2.5 ml), the mixture is subjected to Amberlite XAD-2 column chromatography eluting with methanol-water (1:2). The eluate is concentrated under reduced pressure and lyophilized to yield 3(S)-[8-amino-1(S)-carboxyoctyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid (0.2 g) as colorless powder.

Workup

  1. washeluting with methanol-water (1:2)
  2. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-c63f468be3d24858bd445236d4ea4dac
Source dataset
uspto-grants-1985_10
Patent number
US04548932

Reaction notes

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