Acetic Acid → HCID 13622630, compound

HRID 280952Notes

Reaction equation

HRID 280952 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-f1994329358e4d41860b8af0c3d77a50
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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