1-[2-(4-Heptylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one → 1-[4-Carboxy-2-(4-heptylamino)phenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one

HRID 1635562Notes

Reaction equation

HRID 1635562 reaction equation
[CH3:1][CH2:2][CH2:3][CH:4]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([O:17]C)=[O:16])[CH:12]=[CH:11][C:10]=1[N:19]1[C:23]([CH2:26][OH:27])([CH2:24][OH:25])[CH2:22][CH2:21][C:20]1=[O:28])[CH2:5][CH2:6][CH3:7]>[OH-].[Na+].CO>[C:15]([C:13]1[CH:12]=[CH:11][C:10]([N:19]2[C:23]([CH2:26][OH:27])([CH2:24][OH:25])[CH2:22][CH2:21][C:20]2=[O:28])=[C:9]([NH:8][CH:4]([CH2:5][CH2:6][CH3:7])[CH2:3][CH2:2][CH3:1])[CH:14]=1)([OH:17])=[O:16]

Participants

4

Reactant 1

HCID 120183111-[2-(4-Heptylamino)-4-methoxycarbonylphenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 120183121-[4-Carboxy-2-(4-heptylamino)phenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-oneYield 92.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A suspension of the above ester (0.08 g, 0.2 mmol) in 1 N sodium hydroxide (1.5 mL) and methanol (1 mL) was stirred at ambient tmperature for 12 h. Upon acidification of the reaction mixture with glacial acetic acid, a solid precipitated. The solid was collected by filtration and dried to give 0.07 g (90%) of the title compound, mp 227-229° C.

Workup

  1. customUpon acidification of the reaction mixture with glacial acetic acid, a solid precipitated
  2. filtrationThe solid was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-6afc54c0da9249b99c0c6d7c79122eec
Source dataset
uspto-grants-2003_01
Patent number
US06509359B1

Reaction notes

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