Water → HCID 59361403, compound

HRID 888858Notes

Reaction equation

HRID 888858 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([N:13]1[C:16]([CH3:18])([CH3:17])[C:15](=[O:19])[N:14]1[CH:20]1[CH:27]2[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:29][CH:21]1[CH2:22]3)[CH2:26]2)=[O:12])(=O)C.O.C(=O)(O)[O-].[Na+].O>CO.O1CCCC1>[OH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([N:13]1[C:16]([CH3:17])([CH3:18])[C:15](=[O:19])[N:14]1[CH:20]1[CH:27]2[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:29][CH:21]1[CH2:22]3)[CH2:26]2)=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 46196065HCID 46196065, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 59361403HCID 59361403, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-{[4,4-dimethyl-3-oxo-2-(adamantan-2-yl)-1,2-diazetidin-1-yl]carbonyl}phenyl acetate (15.0 mg, 0.0378 mmol) prepared in Example 137 in methanol-tetrahydrofuran was dropped with saturated sodium bicarbonate water (0.5 mL), and the resultant was stirred at room temperature for 4.5 hours. The reaction solution was added with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified using Preparative Thin-Layer chromatography (hexane:ethyl acetate=2:1), and the title compound (9.80 mg, 73.7%) was obtained as a white crystalline powder.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-f09f7e230db34fc48b09af75875a464a
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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