Acetic Acid → HCID 54098892, compound

HRID 280937Notes

Reaction equation

HRID 280937 reaction equation
Cl.C([O:4][C:5]([C@@H:7]([NH:16][C@@H:17]1[C:23](=[O:24])[N:22]([CH2:25][C:26]([OH:28])=[O:27])[C:21]2[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=2[O:19][CH2:18]1)[CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:6])C.C(O)(=O)C>[OH-].[Na+]>[C:5]([C@@H:7]([NH:16][C@@H:17]1[C:23](=[O:24])[N:22]([CH2:25][C:26]([OH:28])=[O:27])[C:21]2[CH:29]=[CH:30][CH:31]=[CH:32][C:20]=2[O:19][CH2:18]1)[CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)([OH:6])=[O:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 70045131HCID 70045131, compound

Product 1

HCID 54098892HCID 54098892, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In 5 ml of 1N sodium hydroxide solution is dissolved 0.2 g of 3(S)-[1(S)-ethoxycarbonyl-3-(3,4,5,6-tetrahydro-2H-pyran-4-yl)propyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid hydrochloride obtained in Example 43, and the solution is allowed to stand at room temperature for 1 hours. The solution is neutralized with 1.5 ml of acetic acid and purified by Amberlite XAD-2 column chromatography (acetone:water=1:1). The eluate is concentrated under reduced pressure and lyophilized to give 0.16 g of 3(S)-[1(S)-carboxy-3-(3,4,5,6-tetrahydro-2H-pyran-4-yl)propyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid as a colorless powder.

Workup

  1. custompurified by Amberlite XAD-2 column chromatography (acetone:water=1:1)
  2. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-196bfece58b3485f97fc1d279eb4b34f
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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