Succinic anhydride → HCID 70068098, compound

HRID 1066560Notes

Reaction equation

HRID 1066560 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][N:5]1[CH2:10][CH2:9][NH:8][C@@H:7]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:6]1=[O:16].[C:18]1(=[O:24])[O:23][C:21](=[O:22])[CH2:20][CH2:19]1>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH3:15][O:14][C:12]([CH2:11][C@H:7]1[C:6](=[O:16])[N:5]([CH2:4][C:3]([O:2][CH3:1])=[O:17])[CH2:10][CH2:9][N:8]1[C:18](=[O:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[O:13]

Participants

5

Reactant 2

HCID 7922Succinic anhydrideHCID 53955043HCID 53955043, compound

Product 1

HCID 70068098HCID 70068098, compoundYield 66.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of (S)-(3-methoxycarbonylmethyl-2-oxopiperazin-1-yl)acetic acid methyl ester (3.67 g) and succinic anhydride (1.5 g) in dimethylformamide (25 ml) was added 4-dimethylaminopyridine (0.2 g) and the solution was stirred for 3 hours at 60° C. The reaction mixture was concentrated under reduced pressure and the concentrate was purified by means of CHP-20 column chromatography (H2O→50% acetonitrile aqueous solution) to give the titled compound (3.44 g) as a colorless oily substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe concentrate was purified by means of CHP-20 column chromatography (H2O→50% acetonitrile aqueous solution)

Sources & evidence

ORD record
ord-b3e7298a83d940d1ba8838741412378b
Source dataset
uspto-grants-2001_06
Patent number
US06242600B1

Reaction notes

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