Acetic Acid → HCID 13622626, compound

HRID 280947Notes

Reaction equation

HRID 280947 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([OH:27])=[O:26])[C:20]2[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=2[O:18][CH2:17]1)[C:10]([O:12]CC)=[O:11].C(O)(=O)C>[OH-].[Na+]>[NH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C@H:9]([NH:15][C@@H:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([OH:27])=[O:26])[C:20]2[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=2[O:18][CH2:17]1)[C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13622606HCID 13622606, compound

Product 1

HCID 13622626HCID 13622626, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 3(S)-[6-amino-1(S)-ethoxycarbonylhexyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid dihydrochloride (0.35 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 (1:10). The eluate is concentrated under reduced pressure and lyophilized to yield 3(S)-[6-amino-1(S)-carboxyhexyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid (0.17 g) as colorless powder.

Workup

  1. washeluting with methanol-water (1:10)
  2. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f12cb816820e489cae3c2857d56e4781
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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