Benzyl chloroformate → HCID 117861136, compound

HRID 1486277Notes

Reaction equation

HRID 1486277 reaction equation
Cl.[NH2:2][C:3]([CH3:10])([CH2:6][CH2:7][CH2:8][F:9])[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>O1CCCC1.O>[C:4]([C:3]([NH:2][C:18](=[O:19])[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH2:6][CH2:7][CH2:8][F:9])[CH3:10])#[N:5]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformate2×HCID 11430Potassium CarbonateHCID 117858529HCID 117858529, compound

Product 1

HCID 117861136HCID 117861136, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

The crude rac-2-amino-5-fluoro-2-methylpentanonitrile hydrochloride product from Example 76A was initially charged in 185 ml of tetrahydrofuran/water (1:1), and 32.09 g (232.18 mmol) of potassium carbonate and 10.63 g (62.29 mmol) of benzyl chloroformate were added. The reaction mixture (biphasic mixture) was stirred at room temperature overnight. Another 1.93 g (11.33 mmol) of benzyl chloroformate were added to the reaction and the mixture was stirred at room temperature for a further 2 h. Subsequently, the biphasic system was separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were washed once with saturated aqueous sodium chloride solution, and then dried over sodium sulphate, filtered and concentrated by rotary evaporation. The residue was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate gradient=20/1 to 5/1). 11.77 g of the target compound were obtained (72% of theory over two stages, 92% purity).

Workup

  1. stirringthe mixture was stirred at room temperature for a further 2 h
  2. customSubsequently, the biphasic system was separated
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. washThe combined organic phases were washed once with saturated aqueous sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate gradient=20/1 to 5/1)

Sources & evidence

ORD record
ord-5cea7f61f61c4d28b7314dd3ae1aab7b
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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