Hydrochloric Acid → (2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine

HRID 257969Notes

Reaction equation

HRID 257969 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]\[CH2:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])=O)(C)(C)C.Cl.[CH3:33]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]\[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:33])=[O:30])[CH2:10]2)(=[O:15])=[O:16])=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 15670384(2S,4R)-1-t-butoxycarbonyl-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)pyrrolidine

Product 1

HCID 15670385(2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine

Procedure

A solution of (2S,4R)-1-t-butoxycarbonyl-2-[{Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)pyrrolidine (2.90 g) in methanol (50 ml) saturated with hydrogen chloride was stirred at room temperature overnight and the solvent was evaporated in vacuo. The residue was dissolved in chloroform (50 ml) 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 to give (2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine (2.28 g) as a pale brown oil.

Workup

  1. customthe solvent was evaporated in vacuo
  2. dissolutionThe residue was dissolved in chloroform (50 ml)
  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-da6bfc0d2efe43859b4717fb66816686
Source dataset
uspto-grants-1993_11
Patent number
US05264453

Reaction notes

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