Tetrahydrofuran → 4-tert-Butoxycarbonylamino-5-(1-trityl-1H-imidazol-4-yl)-pent-2-enoic acid ethyl ester

HRID 852861노트

반응식

HRID 852861 반응식
C1(P(=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:26]([O:30][C:31](=[O:61])[NH:32][CH:33](C=O)[CH2:34][C:35]1[N:36]=[CH:37][N:38]([C:40]([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=1)([CH3:29])([CH3:28])[CH3:27].[CH2:62]1COCC1>>[CH2:24]([O:23][C:21](=[O:22])[CH:20]=[CH:62][CH:33]([NH:32][C:31]([O:30][C:26]([CH3:28])([CH3:27])[CH3:29])=[O:61])[CH2:34][C:35]1[N:36]=[CH:37][N:38]([C:40]([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)([C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:39]=1)[CH3:25]

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 86591139[1-Formyl-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 694162234-tert-Butoxycarbonylamino-5-(1-trityl-1H-imidazol-4-yl)-pent-2-enoic acid ethyl ester수율 67%

실험 절차

Ethyl (triphenylphosphoranylidene)acetate (1.52 g, 4.37 mmol) and [1-formyl-2-(1-trityl-1H-imidazol-4-yl)-ethyl]-carbamic acid tert-butyl ester (2.1 g, 4.38 mmol) in THF (35 mL) were stirred overnight under argon. The solvent was removed, Et2O added and the solution filtered. The filtrate was concentrated and the residue subject to column chromatography (silica gel, 25% EA/PE, Rf 0.65 50% EA/PE) to afford the title compound (1.6 g, 67%). ESMS 552 (M+H+) Mpt . 1H NMR (300 MHz, CDCl3) δ 1.28 (3H, t, J=7.5), 1.34 (9H, s), 3.01-3.05 (2H, m), 4.19 (2H, q, J=7.05), 4.47-4.57 (1H, m), 6.01 (1H, dd, J=1.5, 15.9), 6.46 (1H, d, J=9.3), 6.86 (1H, s), 6.89 (1H, dd, J=5.1, 15.9), 7.07-7.11 (5H, m), 7.21-7.3 (2H, m), 7.4-7.44 (8H, m), 8.11 (1H, s). 13C NMR (300 MHz, CDCl3) δ 166.14, 155.87, 139.86, 135.20, 132.21, 129.49, 129.70, 129.01, 128.18, 122.33, 121.19, 79.74, 78.78, 60.76, 52.09, 30.12, 28.35, 14.32.

후처리

  1. customThe solvent was removed
  2. additionEt2O added
  3. filtrationthe solution filtered
  4. concentrationThe filtrate was concentrated

출처 및 근거

ORD 기록
ord-d8207051507a47278869bb26d03b066d
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253194B2

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