Ammonium Chloride → (S)-tert-Butyl (3-oxobutan-2-yl)carbamate

HRID 1967300Notes

Reaction equation

HRID 1967300 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]([C:10](=[O:15])N(OC)C)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:17](=O)=O.CC(C)=O.C[Li].C(OCC)C.[Cl-].[NH4+]>O1CCCC1>[CH3:9][C@H:8]([NH:7][C:6](=[O:16])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:10](=[O:15])[CH3:17]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 18522661Acetone cardiceHCID 178467906HCID 178467906, compound

Product 1

HCID 14352057(S)-tert-Butyl (3-oxobutan-2-yl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl{(1S)-1-[methoxy(methyl)carbamoyl]ethyl}carbamate (5.26 g) in tetrahydrofuran (300 mL) was cooled with dry ice/acetone under a nitrogen atmosphere, and 1.6 mol/L-methyllithium/diethyl ether solution (38.8 mL) was added. After stirring at the same temperature for 1.5 hr, saturated aqueous ammonium chloride solution (100 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentration under reduced pressure to give the title compound as a colorless oil (yield: 4.48 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate, and concentration under reduced pressure

Sources & evidence

ORD record
ord-431fd02d2b1e4e689474377c408fa512
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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