(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine → HCID 14772687, compound

HRID 2073262Notes

Reaction equation

HRID 2073262 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[C:24]([O:26][CH3:27])=[O:25])=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]([C:24]([O:26][CH3:27])=[O:25])[CH2:10]2)(=[O:16])=[O:15])=[CH:22][CH:21]=1

Participants

3

Reactant 1

HCID 14772685(2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine

Product 1

HCID 14772687HCID 14772687, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (2S,4R)-1-t-butoxycarbonyl-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine (20 g) in 90% aqueous trifluoroacetic acid was stirred at room temperature for 30 minutes and the solvent was evaporated in vacuo. The residue was dissolved in a mixture of chloroform and methanol (500 ml, 3:1) and the solution was 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)-4-(4-chlorophenylsulfonylamino)-2-methoxycarbonylpyrrolidine (10.7 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of chloroform and methanol (500 ml, 3:1)
  3. washthe solution was washed successively with saturated aqueous sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b7bb76d4ab4a46a4ba184e193797f162
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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