Triphenylphosphine → HCID 69036617, compound

HRID 1726980Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:17][CH3:18])[CH2:5][C:6]1[CH:15]=[C:14]([OH:16])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.[CH3:20][C:21]1[C:26]([CH2:27][CH2:28]O)=[CH:25][CH:24]=[C:23]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)[N:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:17][CH3:18])[CH2:5][C:6]1[CH:15]=[C:14]([O:16][CH2:28][CH2:27][C:26]2[C:21]([CH3:20])=[N:22][C:23]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:37])[F:38])=[CH:32][CH:31]=3)=[CH:24][CH:25]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

0.26 g (1.0 mmol) of the above prepared [rac]-3-(4-hydroxy-naphthalen-2-yl)-2-methoxy-propionic acid methyl ester, 0.30 g (1.05 mmol) of 2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol (see below example 4K]) and 0.31 g (1.20 mmol) of triphenylphosphine were dissolved in 10 ml of THF. The stirred reaction mixture was cooled down to 0° C. and a solution of 0.27 g (1.15 mmol) of di-tert.-butyl azodicarboxylate in 5 ml of THF was added drop by drop and the reaction warmed up to ambient temperature. After 20 hours, the solvent was evaporated and the residue purified by chromatography (SiO2, heptane/EtOAc=9:1 to 1:1) to give 0.45 g of the title compound as light yellow oil.

Workup

customThe stirred reaction mixture
temperaturethe reaction warmed up to ambient temperature
customthe solvent was evaporated
customthe residue purified by chromatography (SiO2, heptane/EtOAc=9:1 to 1:1)

Sources & evidence

ORD record: ord-5513061e4d884e3095b27081b8e49625
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495001B2

Reaction notes

Loading…