HCID 15670378, compound → HCID 15670382, compound

HRID 654163Notes

Reaction equation

HRID 654163 reaction equation
C(OC([N:8]1[CH2:12][C@H:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:10][C@H:9]1/[CH:24]=[CH:25]\[C:26]1[CH:31]=[CH:30][C:29]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][CH:27]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([S:14]([NH:13][C@H:11]2[CH2:12][NH:8][C@H:9](/[CH:24]=[CH:25]\[C:26]3[CH:27]=[CH:28][C:29]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:31]=3)[CH2:10]2)(=[O:15])=[O:16])=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 15670378HCID 15670378, compound

Product 1

HCID 15670382HCID 15670382, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-[(Z)-2-(4-methoxycarbonylphenyl)vinyl]pyrrolidine (15.5 g) in 90% aqueous trifluoroacetic acid (100 ml) was stirred at room temperature for 30 minutes and the solvent was evaporated in vacuo. The residue was suspended in chloroform (200 ml) and the solution was adjusted to pH 8 with saturated aqueous sodium bicarbonate. The organic phase was separated, washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residual solid was collected by filtration to give (2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-2-(4-methoxycarbonylphenyl)vinyl]pyrrolidine (11.9 g) as a white powder.

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. filtrationthe residual solid was collected by filtration

Sources & evidence

ORD record
ord-0766a7bd12b742b2a0956bf42923955b
Source dataset
uspto-grants-1992_07
Patent number
US05130323

Reaction notes

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