Toluene → Boc Cyclopropyl Tryptophan p-Nitrobenzyl Ester

HRID 1249294

반응식

HRID 1249294 반응식
[NH:1]1[CH2:5][CH:4]=[CH:3]N1.[C:6]([O:10][C:11]([NH:13][C:14]1([C:38]([O:40][CH2:41][C:42]2[CH:47]=[CH:46][C:45]([N+:48]([O-:50])=[O:49])=[CH:44][CH:43]=2)=[O:39])[CH2:18][CH:17]([C:19]2C3C(=CC=CC=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)NN1)=[O:12])([CH3:9])([CH3:8])[CH3:7].[CH2:51]1[CH2:53][CH2:52]1.[C:54]1(C)[CH:59]=CC=C[CH:55]=1>>[N+:48]([C:45]1[CH:46]=[CH:47][C:42]([CH2:41][O:40][C:38](=[O:39])[C@H:14]([CH2:18][C:17]2[C:4]3[C:5](=[CH:55][CH:54]=[CH:59][CH:3]=3)[NH:1][CH:19]=2)[N:13]([C:11]([O:10][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:12])[CH:51]2[CH2:53][CH2:52]2)=[CH:43][CH:44]=1)([O-:50])=[O:49]

참가 물질

5

반응물 4

HCID 1140TolueneHCID 6351CyclopropaneHCID 41560032,3-dihydro-1H-pyrazole2회HCID 67901638p-Nitrobenzyl 3-t-Butoxycarbonylamino-5-(N-tosylindol-3-yl)-pyrazoline-3-carboxylate

생성물 1

HCID 86741162Boc Cyclopropyl Tryptophan p-Nitrobenzyl Ester

실험 절차

The pyrazoline, p-nitrobenzyl 3-t-butoxycarbonylamino-5-(N-tosylindol-3-yl)-pyrazoline-3-carboxylate (13), (1 mmole) is suspended in toluene (50 ml) and the mixture is refluxed until its NMR spectrum shows the presence of cyclopropane protons (δ3.0-3.5 and 0.8-1.2 ppm) and the loss of the pyrazoline peak at δ5.0. (2 hr). The solution is evaporated and the residue of Boc cyclopropyl tryptophan p-nitrobenzyl ester (14) is crystallized from ethylacetate-hexane. NMR (DCDl3)δ: 2.7-3.0 (m, 1H, CH), 2.0-2.3 and 1.5-1.7 (m, 2H, CH2).

후처리

  1. temperaturethe mixture is refluxed until its NMR spectrum
  2. custom(2 hr)
  3. customThe solution is evaporated
  4. customthe residue of Boc cyclopropyl tryptophan p-nitrobenzyl ester (14) is crystallized from ethylacetate-hexane

출처 및 근거

ORD 기록
ord-8700355bf63c40489c7a01b92d3c3221
출처 데이터셋
uspto-grants-1986_12
특허 번호
US04629784

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