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

HRID 852861Notes

Reaction equation

HRID 852861 reaction equation
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]

Participants

4

Reactant 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

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-d8207051507a47278869bb26d03b066d
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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