(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate → HCID 11265628, compound

HRID 1243810Notes

Reaction equation

HRID 1243810 reaction equation
CON(C)[C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH3:6].[F:17][C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1.O1CCCC1>O1CCCC1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:4](=[O:15])[C@@H:5]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:12])[CH3:13])[CH3:6])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178420690HCID 178420690, compound

Product 1

HCID 11265628HCID 11265628, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of t-butyl N-{(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamate (50 g) in tetrahydrofuran (700 mL) was gradually added dropwise at 0° C. to a 2.5M 4-fluorophenylmagnesium bromide/tetrahydrofuran solution (300 mL) which had been prepared previously. The mixture was stirred at room temperature for 14 hours, cooled to 0° C., and extracted twice with ether after addition of saturated aqueous sodium bicarbonate. The organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. After removal of the sodium sulfate by filtration, the organic solvent was evaporated off in vacuo. The resulting residue was purified by column chromatography on silica gel (C-300; hexane:ethyl acetate=4:1) to give the title compound.

Workup

  1. customhad been prepared previously
  2. temperaturecooled to 0° C.
  3. extractionextracted twice with ether
  4. additionafter addition of saturated aqueous sodium bicarbonate
  5. washThe organic layer was washed successively with saturated aqueous sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the sodium sulfate
  8. filtrationby filtration
  9. customthe organic solvent was evaporated off in vacuo
  10. customThe resulting residue was purified by column chromatography on silica gel (C-300; hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-9dc6862a05f64a3ea2958bc2d16a13b9
Source dataset
uspto-grants-2006_10
Patent number
US07119107B2

Reaction notes

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