HCID 67863386, compound → HCID 67863365, compound

HRID 2073264Notes

Reaction equation

HRID 2073264 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]([O:28][CH2:29][CH3:30])=[O:27])=O)(C)(C)C>FC(F)(F)C(O)=O>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([S:14]([NH:13][C@H:11]2[CH2:12][NH:8][C@H:9](/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:10]2)(=[O:16])=[O:15])=[CH:22][CH:21]=1

Participants

3

Reactant 1

HCID 67863386HCID 67863386, compound

Product 1

HCID 67863365HCID 67863365, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-[(E)-2-ethoxycarbonylvinyl]pyrrolidine (1.10 g) in 90% aqueous trifluoroacetic acid (10 ml) was stirred at room temperature for 1 hour and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate and the solution was washed successively with saturated aqueous sodium bicarbonate and brine. The organic solution was dried over magnesium sulfate and evaporated in vacuo to give (2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(E)-2-ethoxycarbonylvinyl]pyrrolidine (596 mg) as an oil.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washthe solution was washed successively with saturated aqueous sodium bicarbonate and brine
  4. dry with materialThe organic solution was dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-d6732483353d45a09b983859c24f234c
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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