Ammonium Chloride → HCID 67303368, compound

HRID 888765Notes

Reaction equation

HRID 888765 reaction equation
Cl[CH2:2][C:3]([N:5]([CH:17]1[CH:24]2[CH2:25][CH:20]3[CH2:21][CH:22]([CH2:26][CH:18]1[CH2:19]3)[CH2:23]2)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].CC(C)([O-])C.[K+].[Cl-].[NH4+]>O1CCCC1>[CH:18]12[CH2:26][CH:22]3[CH2:21][CH:20]([CH2:25][CH:24]([CH2:23]3)[CH:17]1[N:5]1[C:3](=[O:4])[CH2:2][N:6]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:19]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 67303134HCID 67303134, compound

Product 1

HCID 67303368HCID 67303368, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, a solution of benzyl 2-(2-chloroacetyl)-2-(adamantan-2-yl)hydrazinecarboxylate (726 mg, 1.93 mmol) in tetrahydrofuran (20 mL) was added at 0° C. with potassium-t-butoxide (238 mg, 2.12 mmol), and the resultant was stirred at the same temperature for 1 hour. The reaction solution was added with a saturated aqueous solution of ammonium chloride, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, the obtained residue was purified using silica gel chromatography (hexane:ethyl acetate=3:1), and benzyl 2-(adamantan-2-yl)-3-oxo-1,2-diazetidine-1-carboxylate (463 mg, 70.4%) was obtained as a colorless oil.

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-e7a44247ce474c228b534e448347a5c0
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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