Ammonium Chloride → Tert-butyl(2-amino-1-cyclopropyl-2-oxoethyl)carbamate

HRID 2406755Notes

Reaction equation

HRID 2406755 reaction equation
CC[N:3]=C=NCCCN(C)C.Cl.C(N(C(C)C)CC)(C)C.[Cl-].[NH4+].[C:24]([O:28][C:29]([NH:31][CH:32]([CH:36]1[CH2:38][CH2:37]1)[C:33](O)=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:25].C(=O)([O-])O.[Na+]>CN(C=O)C.O>[C:24]([O:28][C:29](=[O:30])[NH:31][CH:32]([CH:36]1[CH2:38][CH2:37]1)[C:33]([NH2:3])=[O:34])([CH3:27])([CH3:26])[CH3:25]

Participants

8

Reactant 5

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 224921462-(Tert-butoxycarbonylamino)-2-cyclopropylacetic acid

Product 1

HCID 67776176Tert-butyl(2-amino-1-cyclopropyl-2-oxoethyl)carbamateYield 100.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

H2O (353 mg), WSC.HCl (460 mg), diisopropylethylamine (986 mg), and ammonium chloride (500 mg) were added to a DMF (5 ml) solution containing 2-((tert-butoxycarbonyl)amino)-2-cyclopropyl acetic acid (500 mg) at room temperature, followed by stirring at room temperature for 3 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The resultant was dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, and a white solid of tert-butyl(2-amino-1-cyclopropyl-2-oxoethyl)carbamate (500 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe resultant was dried over anhydrous sodium sulfate
  3. distillationSubsequently, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-390caed6ffd14f1a93036d87e184698c
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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