Methanol → HCID 67863345, compound

HRID 2073267Notes

Reaction equation

HRID 2073267 reaction equation
S(Cl)(Cl)=O.[C:5]([CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:12]\[C@@H:13]1[CH2:17][C@@H:16]([NH:18][S:19]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)(=[O:21])=[O:20])[CH2:15][N:14]1[S:29]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)(=[O:31])=[O:30])([OH:7])=[O:6].[CH3:39]O>>[Cl:38][C:35]1[CH:34]=[CH:33][C:32]([S:29]([N:14]2[CH2:15][C@H:16]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:17][C@H:13]2/[CH:12]=[CH:11]\[CH2:10][CH2:9][CH2:8][C:5]([O:7][CH3:39])=[O:6])(=[O:31])=[O:30])=[CH:37][CH:36]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 67863549HCID 67863549, compound

Product 1

HCID 67863345HCID 67863345, compound

Procedure

Thionyl chloride (0.32 ml) was added to methanol (20 ml) at -78° C. and the solution was stirred at the same temperature for 30 minutes. To the solution was added (2S,4R)-2-[(Z)-5-carboxy-1-pentenyl]-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)pyrrolidine (2.0 g) and the mixture was stirred at room temperature for 2 hours. After removal of the solvent by evaporation in vacuo, the residue was dissolved in chloroform and washed successively with saturated aqueous sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was solidified with ether to give (2S,4R)-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-methoxycarbonyl-1-pentenyl]pyrrolidine (2.0 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customAfter removal of the solvent
  3. customby evaporation in vacuo
  4. dissolutionthe residue was dissolved in chloroform
  5. washwashed successively with saturated aqueous sodium bicarbonate and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-80642bcd0f9640659a97550a33753095
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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