Water → HCID 86642248, compound

HRID 888895Notes

Reaction equation

[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[C:14](=[O:15])[C:13]([CH3:17])([CH3:16])[NH:12]1)[CH2:8]2.C(=O)([O-])[O-].[K+].[K+].[CH2:24]([O:26][C:27](=[O:30])[CH2:28]Br)[CH3:25].O>CN(C)C=O>[CH3:16][C:13]1([CH3:17])[N:12]([CH2:28][C:27]([O:26][CH2:24][CH3:25])=[O:30])[N:11]([CH:2]2[CH:3]3[CH2:4][CH:5]4[CH2:6][CH:7]([CH2:8][CH:1]2[CH2:10]4)[CH2:9]3)[C:14]1=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

Under an argon atmosphere, a solution of 2-(adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one (234 mg, 1.00 mmol) prepared in Process 3 of Example 12 in N,N-dimethylformamide (2 mL) was added with potassium carbonate (277 mg, 2.00 mmol) and ethylbromoacetate (167 mg, 1.00 mmol) at room temperature, and the resultant was stirred at 80° C. for 20 hours. 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 silica gel chromatography (hexane:ethyl acetate=2:1), and ethyl [4,4-dimethyl-3-oxo-2-(adamantan-2-yl)-1,2-diazetidin-1-yl]acetate (190 mg, 59.4%) was obtained as a colorless oil.

Workup

extractionextracted with diethyl ether
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customthe obtained residue was purified

Sources & evidence

ORD record: ord-39deae0a925e48e5a02754ce0b05ee74
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08252781B2

Reaction notes

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