Triphenylphosphine → (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester

HRID 1452698Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:19])[C@H:10]([OH:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:20][C:21]1[CH:26]=[C:25]([C:27]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)([C:32]([F:35])([F:34])[F:33])[C:28]([F:31])([F:30])[F:29])[CH:24]=[CH:23][C:22]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH2:1]([O:8][C:9](=[O:19])[C@@H:10]([O:18][C:22]1[CH:23]=[CH:24][C:25]([C:27]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][C:41]([O:44][CH3:45])=[CH:42][CH:43]=2)([C:28]([F:31])([F:30])[F:29])[C:32]([F:33])([F:34])[F:35])=[CH:26][C:21]=1[CH3:20])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To 1.27 g (4.9 mmol) of (R)-2-hydroxy-3-phenyl-propionic acid benzyl ester in 10 mL of THF were added 1.5 g (3.8 mmol) of 2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenol (example 2) and 1.3 g (4.9 mmol) of triphenylphosphine. The mixture was cooled to 0° C., treated with 0.77 mL (4.9 mmol) of DEAD and stirred at room temperature overnight. The solvent was evaporated and the crude mixture was purified by column chromatography on silica gel with EtOAc/n-heptane 1:4 to yield 1.7 g (71%) of (S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propionic acid benzyl ester as a light yellow oil, MS: 632 (M)+.

Workup

customThe solvent was evaporated
customthe crude mixture was purified by column chromatography on silica gel with EtOAc/n-heptane 1:4

Sources & evidence

ORD record: ord-17f700b2c860408290a9db94fa00f096
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473705B2

Reaction notes

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