Tetrahydrofuran → HCID 69416089, compound

HRID 852849Notes

Reaction equation

HRID 852849 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:25]([O:29][C:30](=[O:54])[NH:31][CH:32](C=O)[CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]([CH2:43][CH:44]=[CH:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH:35]=1)([CH3:28])([CH3:27])[CH3:26].[CH2:55]1COCC1>>[CH3:24][O:23][C:21](=[O:22])[CH:20]=[CH:55][C@H:32]([NH:31][C:30]([O:29][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:54])[CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:36]([CH2:43][CH:44]=[CH:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:35]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 86591137HCID 86591137, compound

Product 1

HCID 69416089HCID 69416089, compoundYield 78%

Procedure

Methyl (triphenylphosphoranylidene)acetate (1.16 g, 3.465 mmol) and {1-formyl-2-[1-(3-phenyl-allyl)-1H-indol-3-yl]-ethyl}-carbamic acid tert-butyl ester (1.4 g, 3.465 mmol) in THF (19 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% EtOAc/petroleum ether) to afford the title compound (1.238 g, 78%), mp 119.3-120.6° C. 1H NMR (CDCl3) δ 7.59 (1H, d, J=7.71 Hz), 7.36-7.01 (9H, m), 6.97 (1H, s), 6.45 (1H, d, J=6.45 Hz), 6.29 (1H, dt, J=5.58 15.93 Hz), 5.88 (1H, d, J=15.93 Hz), 4.82 (2H, d, J=5.4 Hz), 4.69 (1H, br s), 3.65 (3H, s), 3.04 (2H, br s), 1.38 (9H, s), 13C NMR (CDCl3) δ 166.6, 155.1, 148.7, 136.4, 136.1, 132.3, 128.5, 128.2, 127.8, 126.4, 124.7, 121.8, 120.4, 119.3, 119.0, 109.6, 109.5, 79.7, 51.7, 51.5, 48.2, 30.4, 28.2. ISMS: 461 (M+H).

Workup

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

Sources & evidence

ORD record
ord-f4dfabfc16a14706b4cfa47a1871a3ab
Source dataset
uspto-grants-2007_08
Patent number
US07253194B2

Reaction notes

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