4-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid → 4-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 4-methanesulfonyloxy-benzyl ester

HRID 709461Notes

Reaction equation

HRID 709461 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][S:10][CH:11]([C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:28])[Cl:27])=[O:23])[CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.O[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][S:39]([CH3:42])(=[O:41])=[O:40])=[CH:34][CH:33]=1.C1(C2OC(C(F)(F)F)=C(COC(=O)C3C=CC(CC(SCCC4C=CC(F)=CC=4)C(OCC(Cl)(Cl)Cl)=O)=CC=3)N=2)C=CC=CC=1>>[CH3:42][S:39]([O:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][O:18][C:17](=[O:19])[C:16]2[CH:20]=[CH:21][C:13]([CH2:12][CH:11]([S:10][CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:22]([O:24][CH2:25][C:26]([Cl:29])([Cl:27])[Cl:28])=[O:23])=[CH:14][CH:15]=2)=[CH:33][CH:34]=1)(=[O:41])=[O:40]

Participants

4

Reactant 3

HCID 668648234-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acidHCID 85989572Methanesulfonic acid 4-hydroxymethyl-phenyl esterHCID 86650303HCID 86650303, compound

Product 1

HCID 866503054-[2-[2-(4-Fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid 4-methanesulfonyloxy-benzyl esterYield 53.1%

Procedure

The title compound was prepared from 4-[2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxycarbonyl)-ethyl]-benzoic acid (65 mg, 0.135 mmol) and methane-sulfonic acid 4-hydroxymethyl-phenyl ester (27.4 mg, 0.136 mmol) in the same manner as described for 4-[2-[2-(4-fluoro-phenyl)-ethylsulfanyl]-2-(2,2,2-trichloro-ethoxy-carbonyl)-ethyl]-benzoic acid 2-phenyl-5-trifluoromethyl-oxazol-4-ylmethylester. The crude product was purified by flash chromatography using n-heptane/EtOAc 7:3 as the eluent to afford the final product as an oil (47.6 mg, 45%). 1H NMR (400 MHz, CDCl3): δ 7.95-7.97 (d, 2H), 7.47-7.49 (d, 2H), 7.24-7.29 (m, 4H), 7.07-7.08 (m, 2H), 6.91-6.95 (m, 2H), 5.33 (s, 2H), 4.62-4.75 (dd, 2H), 3.55 (t, 1H), 3.25 (t, 1H), 3.13 (s, 3H), 2.79-3.04 (m, 6H). Mass Spectrum: M−H+ 663.04.

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-9d18e5812c4943b3b38f37073d97e954
Source dataset
uspto-grants-2015_11
Patent number
US09181181B2

Reaction notes

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