Water → HCID 59361534, compound

HRID 888897Notes

Reaction equation

HRID 888897 reaction equation
[CH3:1][C:2]1([CH3:20])[N:5]([CH2:6][CH2:7][OH:8])[N:4]([CH:9]2[CH:16]3[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)[C:3]1=[O:19].[H-].[Na+].Cl[C:24]1[N:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1.O>O1CCCC1.CN(C)C=O>[CH3:1][C:2]1([CH3:20])[N:5]([CH2:6][CH2:7][O:8][C:24]2[N:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[N:4]([CH:9]2[CH:10]3[CH2:11][CH:12]4[CH2:13][CH:14]([CH2:15][CH:16]2[CH2:17]4)[CH2:18]3)[C:3]1=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 67302996HCID 67302996, compound

Product 1

HCID 59361534HCID 59361534, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

Under an argon atmosphere, a mixed solution of 4,4-dimethyl-1-(2-hydroxyethyl)-2-(adamantan-2-yl)-1,2-diazetidin-3-one (27.8 mg, 0.100 mmol) in tetrahydrofuran-N,N-dimethylformamide (2:1, 1 mL) was added with sodium hydride (10.0 mg, 0.200 mmol) and 6-chloro-3-pyridine carbonitrile (27.7 mg, 0.200 mmol), and the resultant was stirred at the same temperature for 1 hour. The reaction solution was added with water and extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, the obtained residue was purified using Preparatory Thin-Layer chromatography (hexane:ethyl acetate=1:1), and the title compound (38.1 mg, quant.) was obtained as a white crystalline powder.

Workup

  1. extractionextracted with diethyl ether
  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-3b1cb671873142dd95f2036bfbb450dc
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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