Benzyl chloroformate → HCID 86724664, compound

HRID 1486262Notes

Reaction equation

HRID 1486262 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][F:6])[C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C1CCCCC1.C(OCC)(=O)C>[C:3]([C:2]([NH:1][C:15](=[O:16])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:7])[CH2:5][F:6])#[N:4]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 11007831HCID 11007831, compound

Product 1

HCID 86724664HCID 86724664, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 21867204Cyclohexane ethylacetateSolvent

Procedure

1.34 g (11.83 mmol, about 90%) of rac-2-amino-3-fluoro-2-methylpropanonitrile from Example 53A in 29 ml of THF/water (9/1) were admixed with 5.07 g (36.67 mmol) of potassium carbonate. At 0° C., 1.69 ml (11.83 mmol) of benzyl chloroformate were slowly added dropwise and the reaction mixture was stirred at RT overnight. The solvent was decanted off and the aqueous phase was twice extracted by shaking with THF and then decanting off the THF. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was separated by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate gradient) and the product fractions were concentrated by evaporation on a rotary evaporator. 1.89 g of the target compound were obtained (66% of theory, 97% purity).

Workup

  1. customThe solvent was decanted off
  2. extractionthe aqueous phase was twice extracted
  3. stirringby shaking with THF
  4. customdecanting off the THF
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was separated by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate gradient)
  9. concentrationthe product fractions were concentrated by evaporation on a rotary evaporator

Sources & evidence

ORD record
ord-ef8407f57fe74e2b84c2906fa2f78df9
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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