Trifluoroacetic acid → (+/-) 3-(3,4-Dimethoxyphenyl)sulfanyl-7-phenylheptanoic acid

HRID 1107168Notes

Reaction equation

HRID 1107168 reaction equation
C([O:5][C:6](=[O:30])[CH2:7][CH:8]([S:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=1)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:29][O:28][C:22]1[CH:21]=[C:20]([S:19][CH:8]([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:7][C:6]([OH:30])=[O:5])[CH:25]=[CH:24][C:23]=1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10670305t-Butyl-3-(3,4-dimethoxyphenyl)sulfanyl-7-phenylheptanoate

Product 1

HCID 10619427(+/-) 3-(3,4-Dimethoxyphenyl)sulfanyl-7-phenylheptanoic acidYield 105.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl-3-(3,4-dimethoxyphenyl)sulfanyl-7-phenylheptanoate (14.9 g, 0.03 mol) in CH2Cl2 (150 mL) cooled to 0° C., is added trifluoroacetic acid (30 mL). The solution is allowed to warm to room temperature and stir overnight after which TLC analysis indicated complete reaction. The reaction mixture is concentrated in vacuo and the brown residue is chromatographed on silica gel (pet-ether/EtOAc, 1:1) to afford 11.9 g of (±) 3-(3,4-dimethoxyphenyl)sulfanyl-7-phenylheptanoic acid (91%) as a pale yellow oil. TLC analysis [pet-ether/EtOAc, 1:1, Rf (heptanoate)=0.95, Rf (acid)=0.15]. 1H NMR (300 MHz, CDCl3) δ 1.5-1.65 (m, 6H), 2.55 (m, 4H), 3.30 (t, 1H), 3.85, (d, 6H), 6.80 (d, 1H), 6.98-7.31 (m, 7H) ppm. Mass spectrum (FAB) m/z 374 M+.

Workup

  1. customreaction
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customthe brown residue is chromatographed on silica gel (pet-ether/EtOAc, 1:1)

Sources & evidence

ORD record
ord-0ef1d1a63a794754bd13fae38feb9846
Source dataset
uspto-grants-2000_05
Patent number
US06057369

Reaction notes

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