Water → HCID 59361434, compound

HRID 888879Notes

Reaction equation

HRID 888879 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:11]([CH3:13])([CH3:12])[C:10](=[O:14])[N:9]2[CH:15]2[CH:22]3[CH2:23][CH:18]4[CH2:19][CH:20]([CH2:24][CH:16]2[CH2:17]4)[CH2:21]3)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34].O>ClCCl>[CH3:12][C:11]1([CH3:13])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])=[CH:3][CH:4]=2)[N:9]([CH:15]2[CH:16]3[CH2:24][CH:20]4[CH2:19][CH:18]([CH2:23][CH:22]2[CH2:21]4)[CH2:17]3)[C:10]1=[O:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 46194242HCID 46194242, compound

Product 1

HCID 59361434HCID 59361434, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, a solution of 1-(4-aminophenyl)-4,4-dimethyl-2-(adamantan-2-yl)-1,2-diazetidin-3-one (30.0 mg, 0.0920 mmol) prepared in Example 183 in dichloromethane (1 mL) was added with triethylamine (18.6 mg, 0.184 mmol) and methanesulfonyl chloride (15.8 mg, 0.138 mmol) at room temperature, and the resultant was stirred at the same temperature for 3 hours. The reaction solution was added with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, the obtained residue was purified using Preparative Thin-Layer chromatography (hexane:ethyl acetate=1:1), and the title compound (6.80 mg, 18.3%) was obtained as a brown amorphous solid.

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-eba04509cab14dce879b7704de01fe24
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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