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

HRID 852861ノート

反応式

HRID 852861 の反応式
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]

参加物

4

反応物 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

生成物 1

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

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d8207051507a47278869bb26d03b066d
出典データセット
uspto-grants-2007_08
特許番号
US07253194B2

反応ノート

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