Water → HCID 59361540, compound

HRID 888855Notes

Reaction equation

HRID 888855 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:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>ClCCl.CN(C1C=CN=CC=1)C>[CH3:16][C:13]1([CH3:17])[N:12]([C:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:25])[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

7

Reactant 4

HCID 962WaterHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 673028822-(Adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one

Product 1

HCID 59361540HCID 59361540, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one (33.6 mg, 0.140 mmol) prepared in Process 3 of Example 12 in dichloromethane (2 mL) was added sequentially with benzoyl chloride (40.0 mg, 0.280 mmol), triethylamine (56.6 mg, 0.560 mmol), and DMAP (catalyst amount) at room temperature, and the resultant was stirred at the same temperature for 1.5 hours. The reaction solution was added with water and extracted with chloroform. 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=3:1), and the title compound (40.4 mg, 85.3%) was obtained as a white crystalline powder.

Workup

  1. extractionextracted with chloroform
  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-7cb2c7de038b4738b14322427b2ebd09
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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