Ammonium Chloride → HCID 57577512, compound

HRID 1967306Notes

Reaction equation

HRID 1967306 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].[CH:18]1([Mg]Br)[CH2:20][CH2:19]1.O1CCCC1.[Cl-].[NH4+]>O1CCCC1>[CH:18]1([C:4]([C@@H:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7][CH3:8])=[O:5])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 10422029(S)-2-(Boc-Amino)-N-methoxy-n-methylbutyramideHCID 178420628HCID 178420628, compound

Product 1

HCID 57577512HCID 57577512, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl {(1S)-1-[methoxy(methyl)carbamoyl]propyl}carbamate (14.3 g) in tetrahydrofuran (130 mL) was ice-cooled under a nitrogen atmosphere, and 1.0 mol/L-cyclopropylmagnesium bromide/tetrahydrofuran solution (300 mL) was added. The mixture was stirred at the same temperature for 4.5 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 concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→16%) to give the title compound as a colorless oil (yield: 10.7 g, 94%).

Workup

  1. temperaturecooled under a nitrogen atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated aqueous ammonium chloride solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=0→16%)

Sources & evidence

ORD record
ord-28d54e61c6f04162988eb1eefc5ddffb
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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