Dicyclohexylcarbodiimide → 5-Nitro-isophthalic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 3-allyl ester

HRID 1263603Notes

Reaction equation

HRID 1263603 reaction equation
[CH2:1]([O:4][C:5](=[O:18])[C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9]([OH:11])=[O:10])[CH:2]=[CH2:3].O[N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26].C1CCC(N=C=NC2CCCCC2)CC1>ClCCl>[CH2:1]([O:4][C:5](=[O:18])[C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:15]([O-:17])=[O:16])[CH:14]=1)[C:9]([O:11][N:20]1[C:24](=[O:25])[CH2:23][CH2:22][C:21]1=[O:26])=[O:10])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 206558603-Allyloxycarbonyl-5-nitrobenzoic acid

Product 1

HCID 229860995-Nitro-isophthalic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 3-allyl esterYield 54.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7(a) (10.00 g), N-hydroxysuccinimide (5.04 g) and DCCI (9.03 g) in dichloromethane(400 ml) was stirred at ambient temperature for 3.5 h. The white precipitate which formed was filtered off and the filtrate evaporated under reduced pressure to give a yellow oil. This was purified by flash chromatography eluting with ethyl acetate/hexane (75:25) to give 5-nitro-isophthalic acid 1-(2.5-dioxo-pyrrolidin-1-yl) ester 3-allyl ester (7(b)) as a yellow solid (7.58 g).

Workup

  1. customThe white precipitate which formed
  2. filtrationwas filtered off
  3. customthe filtrate evaporated under reduced pressure
  4. customto give a yellow oil
  5. customThis was purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (75:25)

Sources & evidence

ORD record
ord-8455f08f6a464fa2906666ce7887a45f
Source dataset
uspto-grants-2003_04
Patent number
US06541491B1

Reaction notes

Loading…