Hydrochloric Acid → (2S,4R)-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)-1-(3-pyridylmethyl)pyrrolidine

HRID 257971Notes

Reaction equation

HRID 257971 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:16][N:15]([CH2:17][C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)[C@H:14](/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([O:31]C)=[O:30])[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[C:29]([CH2:28][CH2:27][CH2:26]/[CH:25]=[CH:24]\[C@@H:14]1[CH2:13][C@@H:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH2:16][N:15]1[CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1)([OH:31])=[O:30]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15670386(2S,4R)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]-1-(3-pyridylmethyl)pyrrolidine

Product 1

HCID 6913587(2S,4R)-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)-1-(3-pyridylmethyl)pyrrolidineYield 62.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S,4R)-4-[4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]-1-(3-pyridylmethyl)pyrrolidine (670 mg) in a mixture of methanol (5 ml) and 1N-aqueous sodium hydroxide (3 ml) was stirred at room temperature for 4 hours. The solution was adjusted to pH 5 with 10% hydrochloric acid and extracted with chloroform, and the organic solution was washed with brine. The solution was dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was chromatographed on a silica gel (20 g) column with a mixture of chloroform and methanol (20:1) as an eluent to give (2S,4R)-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)-1-(3-pyridylmethyl)pyrrolidine (408 mg) as a pale yellow amorphous.

Workup

  1. extractionextracted with chloroform
  2. washthe organic solution was washed with brine
  3. dry with materialThe solution was dried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customThe residue was chromatographed on a silica gel (20 g) column with a mixture of chloroform and methanol (20:1) as an eluent

Sources & evidence

ORD record
ord-3fbd968ef6e44419b198d4ba8b054c84
Source dataset
uspto-grants-1993_11
Patent number
US05264453

Reaction notes

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