Methanol → HCID 59852584, compound

HRID 2373857Notes

Reaction equation

CSC.[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@@H:19]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=4)[CH:29]=[CH:30][C:31]=3[O:32]C)=[O:25])[CH2:20][O:21][CH3:22])=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:10]=1[F:11].CO>C(Cl)Cl>[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][C@@H:19]([NH:23][C:24]([C:26]3[CH:27]=[C:28]([C:34]4[CH:35]=[CH:36][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:38][CH:39]=4)[CH:29]=[CH:30][C:31]=3[OH:32])=[O:25])[CH2:20][O:21][CH3:22])=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:10]=1[F:11]

Participants

Conditions

Temperature: -78 °C

Procedure

DMS (13 mg, 0.04 mmol) was added to a solution of 4-Methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-methoxymethyl-ethyl]-amide (24 mg, 0.04 mmol) in 3 mL of anhydrous CH2Cl2, at −78° C. and slowly allowed to come to room temperature and stirred for 2 h. After completion of the reaction, reaction was cooled to −78° C. and 0.5 mL of MeOH was added, solvent was removed under vacuum and the residue was taken in ethyl acetate (4 mL) and washed with aq NaHCO3 solution, water, brine and dried over Na2SO4. Solvent was removed under vacuum and silica gel column chromatography (Ethyl acetate: Hexanes) gave pure 4-Hydroxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid [2-(3′-chloro-4′-fluoro-biphenyl-4-yl)-1-(R)-methoxymethyl-ethyl]-amide (14 mg).

Workup

customto come to room temperature
customAfter completion of the reaction, reaction
customsolvent was removed under vacuum
washwashed with aq NaHCO3 solution, water, brine
dry with materialdried over Na2SO4
customSolvent was removed under vacuum and silica gel column chromatography (Ethyl acetate: Hexanes)

Sources & evidence

ORD record: ord-f75d625773e145a4ab1fbabef51aa422
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459472B2

Reaction notes

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