Sodium Hydroxide → HCID 15670419, compound

HRID 257974Notes

Reaction equation

HRID 257974 reaction equation
[CH2:1]([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]([O:31]C)=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[CH2:1]([N:8]1[CH2:12][C@H:11]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=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])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15670404HCID 15670404, compound

Product 1

HCID 15670419HCID 15670419, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2S,4R)-1-benzyl-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-methoxycarbonyl-1-pentenyl]pyrrolidine (320 mg) in a mixture of methanol (5 ml) and 1N-sodium hydroxide (3 ml) was stirred at room temperature for 3 hours and the volatile solvent was evaporated in vacuo. Water (20 ml) was added to the residue and the aqueous solution was adjusted to pH 7 with 1N-hydrochloric acid. The precipitated solid was collected by filtration and dried in vacuo to give (2S,4R)-1-benzyl-2-[(Z)-5-carboxy-1-pentenyl]-4-(4-chlorophenylsulfonylamino)pyrrolidine (176 mg).

Workup

  1. customthe volatile solvent was evaporated in vacuo
  2. additionWater (20 ml) was added to the residue
  3. filtrationThe precipitated solid was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9bac420bcc014c53aaee2bf55eca6f94
Source dataset
uspto-grants-1993_11
Patent number
US05264453

Reaction notes

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