(+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acid → (+/-)-t-Butyl 3-(3-cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoate

HRID 381389Notes

Reaction equation

HRID 381389 reaction equation
C1(OC2C=C(S)[CH:10]=[CH:11][C:12]=2OC)CCCC1.[CH2:16]([Li])CCC.[CH:21]1([O:26][C:27]2[CH:28]=[C:29]([S:35][CH:36]([CH2:41][CH2:42][CH2:43][CH2:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH2:37][C:38]([OH:40])=[O:39])[CH:30]=[CH:31][C:32]=2[O:33][CH3:34])[CH2:25][CH2:24][CH2:23][CH2:22]1>O1CCCC1.CCCCCC.O>[C:11]([O:39][C:38](=[O:40])[CH2:37][CH:36]([S:35][C:29]1[CH:30]=[CH:31][C:32]([O:33][CH3:34])=[C:27]([O:26][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH:28]=1)[CH2:41][CH2:42][CH2:43][CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)([CH3:10])([CH3:12])[CH3:16]

Participants

7

Reactant 3

HCID 18363145(+/-)-3-(3-Cyclopentyloxy-4-methoxyphenyl)sulfanyl-7-phenylheptanoic acidHCID 183631773-Cyclopentyloxy-4-methoxybenzenethiolHCID 178418339Butyllithium

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A stirred solution of 3-cyclopentyloxy-4-methoxybenzenethiol (0.5 g, Reference Example 2) in anhydrous tetrahydrofuran (20 ml), at 0° C. and under nitrogen, was treated with a solution of n-butyllithium in hexane (0.03 ml, 2.5M). After stirring for 15 minutes the mixture was treated dropwise with a solution of t-butyl 7-phenyl-2-heptenoate (0.39 g, Reference Example 5) in tetrahydrofuran (5 ml) and then the mixture was allowed to warm to room temperature. After stirring at room temperature for 18 hours the reaction mixture was diluted with water (50 ml) and then extracted three times with ether (30 ml). The combined organic extracts were washed with brine (50 ml), then dried over magnesium sulphate and then evaporated. The residual pale yellow oil was subjected to flash chromatography on silica eluting with a mixture of petroleum ether and ethyl acetate (97:3, v/v) to give the title compound (0.5 g) as a colourless oil. NMR (CDCl3): δ1.44 (s,9H), 1.55 (m,8H), 1.95 (m,6H), 2.41 (m,2H), 2.60 (app t,2H), 3.25 (m,1H), 3.81 (s,3H) 4.74 (m,1H), 6.79 (d, 1H), 6.99 (dd,2H), 7.10-7.30 (m,5H). Mass spectrum (FAB): m/z 484 M+.

Workup

  1. stirringAfter stirring at room temperature for 18 hours the reaction mixture
  2. extractionextracted three times with ether (30 ml)
  3. washThe combined organic extracts were washed with brine (50 ml)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. additionThe residual pale yellow oil was subjected to flash chromatography on silica eluting with a mixture of petroleum ether and ethyl acetate (97:3

Sources & evidence

ORD record
ord-cbcd963a087144dcab8345990b3d2efd
Source dataset
uspto-grants-2001_10
Patent number
US06306873B1

Reaction notes

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