HCID 66865303, compound → HCID 66865394, compound

HRID 1192905Notes

Reaction equation

HRID 1192905 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][C:6]1([NH:21][S:22]([C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:10][CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH2:7]1)[CH3:2]>CCO.[Pd]>[CH2:31]([C:28]1[CH:29]=[CH:30][C:25]([S:22]([NH:21][C:6]2([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:36])[CH2:10][CH2:9][NH:8][CH2:7]2)(=[O:23])=[O:24])=[CH:26][CH:27]=1)[CH2:32][CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 1

HCID 66865303HCID 66865303, compound

Product 1

HCID 66865394HCID 66865394, compoundYield 62.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl 3-(2-ethoxy-2-oxoethyl)-3-(4-pentylphenylsulfonamido)-pyrrolidine-1-carboxylate (120 mg, 0.23 mmol) in EtOH (5 mL) was purged with nitrogen and Pd/C (25 mg) was added and the flask was purged with hydrogen and stirred for 24 h. The mixture was filtered through celite and concentrated. The residue was dissolved into H2O and lyophilized to give the title compound as a white solid (55 mg, 62%). MS ESI 383.2 [M+H]+, calcd for [C19H30N2O4S+H]+ 383.19.

Workup

  1. additionwas added
  2. customthe flask was purged with hydrogen
  3. filtrationThe mixture was filtered through celite
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved into H2O

Sources & evidence

ORD record
ord-2654ce463d6f4e6a94e349ef2fdbc070
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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