Benzyl chloroformate → HCID 131731730, compound

HRID 2401276Notes

Reaction equation

HRID 2401276 reaction equation
Cl.[NH2:2][C@@H:3]([C@@H:6]([F:9])[CH2:7][CH3:8])[CH2:4][OH:5].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(=O)([O-])O.[Na+]>C1COCC1.O>[CH2:20]([O:19][C:17](=[O:18])[NH:2][C@@H:3]([C@@H:6]([F:9])[CH2:7][CH3:8])[CH2:4][OH:5])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86705175HCID 86705175, compound

Product 1

HCID 131731730HCID 131731730, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (2R,3S)-2-amino-3-fluoropentan-1-ol hydrochloride (2.0 g) in THF (60 mL) was cooled in ice, a solution of potassium carbonate (4.4 g) in water (6 mL) and a solution of benzyl chloroformate (2.4 g) in THF (6 mL) were added thereto, and the mixture was stirred at room temperature overnight. Saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate and drying over anhydrous magnesium sulfate. After the desiccant was filtered off, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=88:12-0:100) to afford benzyl[(2R,3S)-3-fluoro-1-hydroxypentan-2-yl]carbamate (2.5 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialdrying over anhydrous magnesium sulfate
  3. filtrationAfter the desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate=88:12-0:100)

Sources & evidence

ORD record
ord-f4696f78965941d5b2111de1487c153a
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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