Benzyl chloroformate → HCID 67273731, compound

HRID 2193529Notes

Reaction equation

HRID 2193529 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][C:15]=2[F:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]>C(OCC)(=O)C.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])=[CH:16][C:15]=2[F:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 10387Benzyl chloroformateHCID 67274080HCID 67274080, compound

Product 1

HCID 67273731HCID 67273731, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4 g of (3R)-3-(2-fluoro-4-nitro-phenyl-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester (12.29 mmol) in 100 ml ethyl acetate and 50 ml methanol were added 1 g of Pd/C 10%. The suspension was stirred under hydrogen. The reaction was monitored by TLC. The catalyst was filtered, the filtrate evaporated to dryness, and the residue was dissolved in 100 ml of acetone. 25 ml of a saturated solution of sodium bicarbonate was added, than a 0° C. 3.63 ml of benzyl chloroformate (25.8 mmol). The reaction was stirred over night at rt and monitored by TLC. The acetone was evaporated, the water layer extracted twice with ethyl acetate, the org layer washed with water and brine, dried over Mg sulfate, filtered and the filtrate evaporated to dryness. The residue was purified by chromatography, using a 1/1 ethyl acetate/hexane mixture as eluent.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated to dryness
  3. dissolutionthe residue was dissolved in 100 ml of acetone
  4. addition25 ml of a saturated solution of sodium bicarbonate was added, than a 0° C
  5. stirringThe reaction was stirred over night at rt
  6. customThe acetone was evaporated
  7. extractionthe water layer extracted twice with ethyl acetate
  8. washthe org layer washed with water and brine
  9. dry with materialdried over Mg sulfate
  10. filtrationfiltered
  11. customthe filtrate evaporated to dryness
  12. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-6a5e57db7a104f9698279036fdfc569d
Source dataset
uspto-grants-2012_12
Patent number
US08329908B2

Reaction notes

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