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

HRID 1263603

Reaktionsgleichung

Reaktionsgleichung von HRID 1263603
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 229860995-Nitro-isophthalic acid 1-(2,5-dioxo-pyrrolidin-1-yl) ester 3-allyl esterAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-8455f08f6a464fa2906666ce7887a45f
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541491B1

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