Benzyl chloroformate → HCID 86724734, compound

HRID 1486265Notes

Reaction equation

HRID 1486265 reaction equation
[NH2:1][C:2]([CH3:11])([CH2:5][CH2:6][C:7]([F:10])([F:9])[F:8])[C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>O1CCCC1.O>[C:3]([C:2]([NH:1][C:19](=[O:20])[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:5][CH2:6][C:7]([F:8])([F:9])[F:10])[CH3:11])#[N:4]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 90232391HCID 90232391, compound

Product 1

HCID 86724734HCID 86724734, compoundYield 70.9%

Reagents, catalysts & solvents 1

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

Procedure

8.7 g (52.36 mmol) of rac-2-amino-5,5,5-trifluoro-2-methylpentanonitrile from Example 60A were initially charged in 128 ml of tetrahydrofuran/water=9/1, and 22.43 g (162.3 mmol) of potassium carbonate were added. At 0° C., 8.93 g (52.36 mmol) of benzyl chloroformate were added dropwise. Then the mixture was allowed to warm up gradually to room temperature and stirred at room temperature overnight. The supernatant solvent was decanted off, the residue was twice stirred with 100 ml each time of tetrahydrofuran, and then the supernatant solvent was decanted off each time. The combined organic phases were concentrated and the crude product was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate gradient 9/1 to 4/1). 11.14 g of the title compound were obtained (68% of theory).

Workup

  1. additionwere added
  2. customThe supernatant solvent was decanted off
  3. stirringthe residue was twice stirred with 100 ml each time of tetrahydrofuran
  4. customthe supernatant solvent was decanted off each time
  5. concentrationThe combined organic phases were concentrated
  6. customthe crude product was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate gradient 9/1 to 4/1)

Sources & evidence

ORD record
ord-b739c13598ff42359ffaa8b54002b857
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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