Ammonium Chloride → HCID 45091960, compound

HRID 1967302Notes

Reaction equation

HRID 1967302 reaction equation
CON(C)[C:4]([C@@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH3:8])=[O:5].[C:18](=O)=O.CC(C)=O.C[Li].C(OCC)C.[Cl-].[NH4+]>O1CCCC1>[CH2:7]([C@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[C:4](=[O:5])[CH3:18])[CH3:8]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 10422029(S)-2-(Boc-Amino)-N-methoxy-n-methylbutyramideHCID 18522661Acetone cardiceHCID 178467906HCID 178467906, compound

Product 1

HCID 45091960HCID 45091960, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl {(1S)-1-[methoxy(methyl)carbamoyl]propyl}carbamate (15.0 g) in tetrahydrofuran (150 mL) was cooled using dry ice/acetone under a nitrogen atmosphere, and 1.0 mol/L-methyllithium/diethyl ether solution (300 mL) was added. The mixture was stirred at the same temperature for 4 hr, saturated aqueous ammonium chloride solution (300 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine, dried over anhydrous magnesium sulfate, and concentration under reduced pressure to give the title compound as a colorless oil (yield: 12.75 g).

Workup

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

Sources & evidence

ORD record
ord-cad7c511be6f425b8d5ff9af0e37b100
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

Loading…