Ammonium Chloride → HCID 57577520, compound

HRID 1173632Notes

Reaction equation

HRID 1173632 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(=O)=O.[CH3:20][C:21]([CH3:23])=O.C1([Mg]Br)CC1.O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6](=[O:16])[NH:7][C@@H:8]([CH3:9])[C:10]([CH:21]1[CH2:23][CH2:20]1)=[O:15])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 18522661Acetone cardiceHCID 178420628HCID 178420628, compound

Product 1

HCID 57577520HCID 57577520, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl{(1S)-1-[methoxy(methyl)carbamoyl]ethyl}carbamate (10.0 g) in tetrahydrofuran (110 mL) was cooled using dry ice/acetone under a nitrogen atmosphere, and 1.0 mol/L-cyclopropylmagnesium bromide/tetrahydrofuran solution (100 mL) was added. The mixture was warmed to room temperature and stirred for 5 hr, saturated aqueous ammonium chloride solution (200 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%) to give the title compound as a yellow oil (yield: 3.65 g, 40%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→30%)

Sources & evidence

ORD record
ord-55659bbb8e1048c783dc41759555d1e1
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

Loading…