(4-Nitrophenyl)acetic acid → di t-butyl 4-nitrobenzylcarbonyl-L-glutamate

HRID 2258405

Reaktionsgleichung

Reaktionsgleichung von HRID 2258405
[OH:1][N:2]1C2C=CC=CC=2N=N1.[N+]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=O)=[CH:16][CH:15]=1)([O-])=O.[C:24]([O:28][C:29](=[O:41])[C@H:30]([CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[NH2:31])([CH3:27])([CH3:26])[CH3:25].C1(N=C=NC2CCCCC2)CCCCC1.CN(C)C=[O:60]>>[N+:2]([CH:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][C@@H:30]([C:29]([O:28][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:41])[NH:31][C:21]([CH2:20][C:17]1[CH:16]=[CH:15][CH:14]=[CH:19][CH:18]=1)=[O:23])([O-:1])=[O:60]

Komponenten

6

Edukt 5

HCID 4661(4-Nitrophenyl)acetic acidHCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 208637L-Glutamic acid di-tert-butyl ester

Produkt 1

HCID 86748613di t-butyl 4-nitrobenzylcarbonyl-L-glutamateAusbeute 77 %

Versuchsvorschrift

1-Hydroxybenzotriazole (4.05 g) was added to a solution of 4-nitrophenyl acetic acid (5.4 g) in dimethylformamide (75 ml). L-Glutamic acid di tert-butyl ester (7.77 g) and then dicyclohexylcarbodiimide (6.2 g) were added to the mixture. The mixture was then stirred for 18 hr at ambient temperature. The mixture was filtered and the filtrate washed with saturated sodium bicarbonate solution, water and 0.5 m hydrochloric acid and then dried and evaporated to dryness. The residue was chromatographed on silica gel by eluting with hexane/ethyl acetate (2:1) to give di t-butyl 4-nitrobenzylcarbonyl-L-glutamate as an oil 9.7 g (77%).

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe filtrate washed with saturated sodium bicarbonate solution, water and 0.5 m hydrochloric acid
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel
  6. washby eluting with hexane/ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-9e64f68fc8d54e62a2407108e26468ec
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05660829

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