P-Toluic Acid → 2,5-Pyrrolidinedione, 1-[(4-methylbenzoyl)oxy]-

HRID 3671

Reaction equation

HRID 3671 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].C(N(CC)CC)C.[C:16]1([CH3:25])[CH:21]=[CH:20][C:19]([C:22](O)=[O:23])=[CH:18][CH:17]=1.P(Cl)(OCC)(OCC)=O>C(OCC)(=O)C>[C:6]1(=[O:7])[N:2]([O:1][C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:25])=[CH:17][CH:18]=2)=[O:23])[C:3](=[O:8])[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 7470P-Toluic AcidHCID 8471TriethylamineHCID 13139Diethyl chlorophosphateHCID 80170N-Hydroxysuccinimide

Product 1

HCID 64224042,5-Pyrrolidinedione, 1-[(4-methylbenzoyl)oxy]-

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Analogous example 3 2,76 g (0.024 mol) of N-hydroxysuccinimide and 5.06 g (0,050 mol) of triethylamine were initially introduced into 5 ml of ethyl acetate and stirred at room temperature. 2.72 g (0.020 mol) of solid 4-toluic acid were added to this suspension in the course of 5 min. and then a solution of 3.47 g (0,020 mol) of diethyl chlorophosphate was added dropwise in the course of 20 min., the reaction mixture warming to about 35° C. The mixture was stirred at room temperature for 3 hours until the reaction was complete. The further proceeding was performed analogous example 3. 2.8 g of crude 4-toluic acid succinimidyl ester were isolated.

Workup

  1. temperaturethe reaction mixture warming to about 35° C
  2. stirringThe mixture was stirred at room temperature for 3 hours until the reaction

Sources & evidence

ORD record
ord-dd19c881eac941828954e215ecddc363
Source dataset
uspto-grants-1998_03
Patent number
US05734064

Linked notes

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