Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → HCID 118460903, compound

HRID 63707Notes

Reaction equation

HRID 63707 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].[CH2:26]([O:28][CH2:29][C:30]1[N:31]([CH2:65][C:66]([OH:69])([CH3:68])[CH3:67])[C:32]2[C:41]3[CH:40]=[CH:39][C:38]([CH:42]=O)=[CH:37][C:36]=3[N:35]=[C:34]([NH:44][C:45]([C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:33]=2[N:64]=1)[CH3:27]>ClCCl>[CH2:26]([O:28][CH2:29][C:30]1[N:31]([CH2:65][C:66]([OH:69])([CH3:68])[CH3:67])[C:32]2[C:41]3[CH:40]=[CH:39][C:38](/[CH:42]=[CH:6]/[C:1]([O:3][CH2:4][CH3:5])=[O:2])=[CH:37][C:36]=3[N:35]=[C:34]([NH:44][C:45]([C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:33]=2[N:64]=1)[CH3:27]

Participants

4

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 118451579HCID 118451579, compound

Product 1

HCID 118460903HCID 118460903, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Carbethoxymethylene)triphenylphosphorane (422 mg, 1.21 mmol) was added to a solution of 2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-4-(tritylamino)-1H-imidazo[4,5-c]quinoline-7-carbaldehyde (472 mg, 808 μmol) in dichloromethane (8 mL) under argon. The reaction mixture was stirred for 20 h at room temperature and concentrated in vacuo. Crystallization from dichloromethane and diethyl ether afforded the title compound (0.399 g, 75%) as white solid, LC-MS (UV peak area, ESI) 89%, 655.4 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customCrystallization from dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-738e7f8a4dc74dc89f48de76f2f16028
Source dataset
uspto-grants-2016_09
Patent number
US09447097B2

Reaction notes

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