1-[4-Methoxycarbonyl-2-(3-pentylamino)phenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one → 1-[4-Carboxy-2-(3-Pentylamino)Phenyl]-5,5'-Di(Hydroxymethyl)Pyrrolidin-2-One

HRID 1635559Notes

Reaction equation

HRID 1635559 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([CH2:18][OH:19])([CH2:16][OH:17])[CH2:14][CH2:13][C:12]2=[O:20])=[C:7]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:6]=1)=[O:4]>[OH-].[Na+]>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([CH2:18][OH:19])([CH2:16][OH:17])[CH2:14][CH2:13][C:12]2=[O:20])=[C:7]([NH:21][CH:22]([CH2:25][CH3:26])[CH2:23][CH3:24])[CH:6]=1)([OH:4])=[O:2]

Participants

3

Reactant 1

HCID 104990031-[4-Methoxycarbonyl-2-(3-pentylamino)phenyl]-5,5-bis-(hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 4445081-[4-Carboxy-2-(3-Pentylamino)Phenyl]-5,5'-Di(Hydroxymethyl)Pyrrolidin-2-OneYield 75.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of the above ester (0.07 g, 0.19 mmol) in 1 N sodium hydroxide (1 mL) was stirred at ambient temperature for 12 h. Upon acidification of the reaction mixture with glacial acetic acid, a solid precipitated. This solid was collected by filtration and dried to give 0.05 g (75%) of the title compound as a white solid, mp 220-221° C.

Workup

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

Sources & evidence

ORD record
ord-8038fc71c5a54a42830fe8247384c08a
Source dataset
uspto-grants-2003_01
Patent number
US06509359B1

Reaction notes

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