Succinic anhydride → HCID 70230303, compound

HRID 1066564Notes

Reaction equation

HRID 1066564 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C@@H:10]([CH2:14]C(OC)=O)[C:9]1=[O:19])([CH3:4])([CH3:3])[CH3:2].[C:21]1(=[O:27])[O:26][C:24](=[O:25])[CH2:23][CH2:22]1>CN(C)C=O>[C:1]([O:5][C:6]([CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:24](=[O:25])[CH2:23][CH2:22][C:21]([OH:26])=[O:27])[C@:10]([CH3:14])([C:6]([O:5][CH3:1])=[O:20])[C:9]1=[O:19])=[O:20])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 10636945HCID 10636945, compound

Product 1

HCID 70230303HCID 70230303, compoundYield 192.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (S)-(3-methoxycarbonylmethyl-2-oxo-piperazin-1-yl)acetic acid tert-butyl ester (1.0 g) and succinic anhydride (0.7 g) in dimethylformamide (15 ml) was stirred for 5 hours at room temperature. The reaction mixture was concentrated under reduced pressure. The concentrate was dissolved in water (10 ml) and purified by means of CHP-20 column chromatography (H2O→30% acetonitrile aqueous solution) to give the titled compound (1.3 g) as a colorless oily product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe concentrate was dissolved in water (10 ml)
  3. custompurified by means of CHP-20 column chromatography (H2O→30% acetonitrile aqueous solution)

Sources & evidence

ORD record
ord-a8db85a73b60474b886c746cb2aba2ab
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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