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

HRID 861217

반응식

HRID 861217 반응식
[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]

참가 물질

6

반응물 5

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

생성물 1

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

실험 절차

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%). NMR: 8.2(d)2H; 7.45(d)2H; 6.45(d)1H; 4.45(m)1H; 3.15(s)2H; 2.1(m)4H; 1.4(d)9H; 1.35(s)9H.

후처리

  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)

출처 및 근거

ORD 기록
ord-796d4fcfc51c40ed8eb9649c8cc9f03d
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714148

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