Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 58467989, compound

HRID 1879391Notes

Reaction equation

HRID 1879391 reaction equation
[C:1]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:3][CH2:4][CH3:5])=[O:2].[F:26][C:27]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=1[C@@H:34]1[CH2:44][CH2:43][C:42](=O)[C:37]2=[N:38][CH:39]=[CH:40][CH:41]=[C:36]2[C@H:35]1[NH:46][C:47](=[O:53])[O:48][C:49]([CH3:52])([CH3:51])[CH3:50]>C1(C)C=CC=CC=1>[C:49]([O:48][C:47]([NH:46][C@@H:35]1[C:36]2[C:37](=[N:38][CH:39]=[CH:40][CH:41]=2)/[C:42](=[CH:6]/[C:1]([O:3][CH2:4][CH3:5])=[O:2])/[CH2:43][CH2:44][C@H:34]1[C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([F:33])[C:27]=1[F:26])=[O:53])([CH3:51])([CH3:52])[CH3:50]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 58468004HCID 58468004, compound

Product 1

HCID 58467989HCID 58467989, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (carbethoxymethylene)triphenylphosphorane (0.214 g, 0.614 mmol) and tert-butyl (5S,6S)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-5-ylcarbamate (0.199 g, 0.512 mmol) in toluene (5 mL) was heat to reflux for 18 h. The solvent was removed via vacuum and the crude residue was loaded onto a silica gel column directly. Purification was performed by elution with ethyl acetate in hexane from 0 to 65% to afford the desired product (138 mg, 59%): MS(ESI)[M+H+]=459.22; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.53 (1H, dd, J=4.8, 1.3 Hz), 7.70 (1H, d, J=7.5 Hz), 7.32 (1H, dd, J=7.8, 4.8 Hz), 7.15-7.24 (1H, m), 7.05-7.13 (2H, m), 6.39 (1H, t, J=2.3 Hz), 5.21-5.31 (1H, m), 4.89-4.99 (1H, m), 4.19 (2H, q, J=7.1 Hz), 3.32-3.43 (1H, m), 3.17-3.32 (1H, m), 3.12 (1H, d, J=2.3 Hz), 1.87 (2H, d, J=4.5 Hz), 1.14-1.38 (13H, m).

Workup

  1. temperaturewas heat
  2. temperatureto reflux for 18 h
  3. customThe solvent was removed via vacuum
  4. customPurification
  5. washwas performed by elution with ethyl acetate in hexane from 0 to 65%

Sources & evidence

ORD record
ord-3aa3708374c44c96a7c0c27256aa8f52
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

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