Benzyl chloroformate → HCID 90115137, compound

HRID 1624113Notes

Reaction equation

HRID 1624113 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[CH2:4][CH2:5][CH2:6][C@@H:7]([C:9]([O:11][CH3:12])=[O:10])[NH2:8].C(=O)([O-])[O-].[K+].[K+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O.C1COCC1.O>[CH2:25]([O:24][C:22]([NH:8][C@H:7]([C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][CH2:4][C:3]([F:13])([F:14])[F:2])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 90115251HCID 90115251, compound

Product 1

HCID 90115137HCID 90115137, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

3.77 g (14.4 mmol, purity about 90%) of rac-methyl 6,6,6-trifluoronorleucinate hydrochloride Example 99A were initially charged in 212 ml of water/THF (8:1), and 6.17 g (44.6 mmol) of potassium carbonate were added. The reaction mixture was cooled to 0° C., 2.68 ml (15.8 mmol) of benzyl chloroformate were slowly added dropwise and the mixture was then stirred at RT overnight. The mixture was diluted with 100 ml of water and extracted three times with dichloromethane. The combined organic phases were dried over sodium sulphate, filtered off and concentrated. The residue was purified by silica gel chromatography (cyclohexane/ethyl acetate 4:1). This gave 3.64 g (76% of theory, purity 100%) of the target compound.

Workup

  1. extractionextracted three times with dichloromethane
  2. dry with materialThe combined organic phases were dried over sodium sulphate
  3. filtrationfiltered off
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (cyclohexane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-aa71375781564b9aa0d145544429833d
Source dataset
uspto-grants-2014_07
Patent number
US08778964B2

Reaction notes

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