Ammonium Chloride → HCID 57577520, compound

HRID 1967304Notes

Reaction equation

HRID 1967304 reaction equation
CON(C)[C:4]([C@@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:7])=[O:5].C(=O)=O.[CH3:20][C:21]([CH3:23])=O.C1([Mg]Br)CC1.O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[CH:21]1([C:4](=[O:5])[C@@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH3:7])[CH2:23][CH2:20]1

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 {(15)-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-c4cec9acab66457aaa02ab1be72bcfe0
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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