Dicyclohexylcarbodiimide → 1-{[(4-Chloro-1H-pyrrol-2-yl)carbonyl]oxy}pyrrolidine-2,5-dione

HRID 1172792Notes

Reaction equation

HRID 1172792 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([OH:9])=[O:8])[NH:5][CH:6]=1.O[N:11]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]1=[O:17].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][N:11]2[C:15](=[O:16])[CH2:14][CH2:13][C:12]2=[O:17])=[O:8])[NH:5][CH:6]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 71308424-chloro-1H-pyrrole-2-carboxylic acid

Product 1

HCID 866334231-{[(4-Chloro-1H-pyrrol-2-yl)carbonyl]oxy}pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloro-1H-pyrrole-2-carboxylic acid (1 eq), N-hydroxysuccinimide (1 eq) and DCC (1.05 eq) in dry THF was stirred at RT for 12 h. The solid urea was filtered off and washed with THF. The filtrate was evaporated under reduced pressure and the resulting crude was purified by on silica gel eluting with petrol ether/EtOAc to obtain the title compound as a white-off powder. 1H NMR (400 MHz, DMSO-d6) δ: 12.87 (1H, br. S), 7.50-7.45 (1H, m), 7.16-7.12 (1H, m), 2.87 (4H, s).

Workup

  1. filtrationThe solid urea was filtered off
  2. washwashed with THF
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe resulting crude was purified by on silica gel eluting with petrol ether/EtOAc

Sources & evidence

ORD record
ord-4a70f3a8a7674b38925388580d451267
Source dataset
uspto-grants-2010_11
Patent number
US07834015B2

Reaction notes

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