Trifluoroacetic acid → (+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acid

HRID 381388Notes

Reaction equation

HRID 381388 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([S:15][CH:16]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([S:15][CH:16]([CH2:25][CH2:26][CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:17][C:18]([OH:20])=[O:19])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18363156(+/-)-t-Butyl 3-(3-cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoate

Product 1

HCID 18363145(+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acidYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (±)-t-butyl 3-(3-cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoate [0.5 g, Reference Example 1(a)] in dichloromethane (20 ml), at 0° C., was treated with trifluoroacetic acid (4 ml). The solution was allowed to warm to room temperature and then stirred for 18 hours. The reaction mixture was evaporated and the brown residue subjected to flash chromatography on silica eluting with a mixture of petroleum ether and ethyl acetate (1:1, v/v) to give the title compound (0.4 g) as a colourless oil. NMR (CDCl3): δ1.60 (m,8H), 1.90 (m,6H), 2.60 (m,4H), 3.28 (m,1H), 3.82 (s,3H), 4.74 (m,1H), 6.78 (d,1H), 7.00-7.38 (m,7H). Mass spectrum (FAB): m/z 428 M+.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe brown residue subjected to flash chromatography on silica eluting with a mixture of petroleum ether and ethyl acetate (1:1

Sources & evidence

ORD record
ord-6ed3b1d736314d91ab4f594b3873bbee
Source dataset
uspto-grants-2001_10
Patent number
US06306873B1

Reaction notes

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