1,1-Dichloroethane → HCID 20741395, compound

HRID 457408Notes

Reaction equation

HRID 457408 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].ClC(Cl)C.[C:16]([O:20][C:21]([NH:23][CH:24]([C@H:30]1[CH2:34][CH2:33][N:32]([C@@H](C2C=CC=CC=2)C)[C:31]1=O)[C:25]1[O:26][CH:27]=[CH:28][CH:29]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>>[C:16]([O:20][C:21]([NH:23][CH:24]([C@@H:30]1[CH2:34][CH2:33][N:32]([C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH2:31]1)[C:25]1[O:26][CH:27]=[CH:28][CH:29]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

4

Reactant 3

HCID 63651,1-DichloroethaneHCID 10387Benzyl chloroformateHCID 18439397HCID 18439397, compound

Product 1

HCID 20741395HCID 20741395, compoundYield 74.2%

Procedure

In an atmosphere of nitrogen, benzyl chloroformate (761 μl, 5.31 mmol) was added dropwise to a dichloroethane solution (15 ml) of 3-(R)-[1-tert-butoxycarbonylamino-1-(2-furyl)methyl]-1-[1-(R)-phenylethyl]-2-pyrrolidone [F1] (658 mg, 1.77 mmol) under ice-cooling and then the m was heated under refulx for 30 hours. After evaporation of the solvent under a reduced pressure, the residue was applied to a silica gel column chromatography. By eluting with chloroform to chloroform:methanol (97:3), 526 mg (74%) of the title compound was obtained as white crystals.

Workup

  1. temperaturecooling
  2. temperaturethe m was heated under refulx for 30 hours
  3. customAfter evaporation of the solvent under a reduced pressure
  4. washBy eluting with chloroform to chloroform:methanol (97:3)

Sources & evidence

ORD record
ord-d629644913984d1ebcf431932d1a327f
Source dataset
uspto-grants-2007_03
Patent number
US07186843B2

Reaction notes

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