Hydrochloric Acid → 2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-3-(4-hydroxymethyl-phenyl)-propionic acid 2,2,2-trichloro-ethyl ester
Reaction equation
[Cl:1][C:2]([Cl:35])([Cl:34])[CH2:3][O:4][C:5](=[O:33])[CH:6]([S:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](C)(C)[O:15][SiH2]C(C)(C)C)=[CH:10][CH:9]=1.B(F)(F)F.CCOCC.Cl>C(#N)C.O>[Cl:34][C:2]([Cl:1])([Cl:35])[CH2:3][O:4][C:5](=[O:33])[CH:6]([S:23][CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=1)[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][OH:15])=[CH:12][CH:13]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-[4-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-propionic acid 2,2,2-trichloro-ethyl ester (5.47 g, 9.43 mmol) in anhydrous acetonitrile (200 mL) was dropwise added BF3×Et2O (1.10 mL, 9.43 mmol) at 0° C. The mixture was stirred for 30 min. 2N aq. HCl (50 mL) and H2O (100 mL) were added and the mixture was extracted with DCM. The combined organic layers were dried (MgSO4) and evaporated to give the crude product which was purified by flash chromatography using DCM/MeOH 95:5 as the eluent. The product was obtained as an (3.62 g, 82.5%). 1H NMR (400 MHz, CDCl3): δ 7.19 (d, 2H), 7.10 (d, 2H), 7.01 (m, 2H), 6.87 (t, 2H), 4.65 (d, 1H), 4.56 (m, 3H), 3.48 (dd, 1H), 3.12 (dd, 1H), 2.73-2.91 (m, 5H). Mass Spectrum: M−H+ 464.90.
Workup
- customat 0° C
- extractionthe mixture was extracted with DCM
- dry with materialThe combined organic layers were dried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-cb6c7dab94044561b11823284c608196
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181181B2
Reaction notes
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