Water → HCID 86642718, compound

HRID 1361098Notes

Reaction equation

I[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:6]([S:10]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[C:25]([OH:35])[CH:24]=2)=[CH:16][C:15]=1[O:36][CH3:37])(=[O:12])=[O:11])[CH2:7][CH2:8][CH3:9].C(=O)([O-])[O-].[K+].[K+].O>C(C(C)=O)C>[CH2:6]([S:10]([O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[C:25]([O:35][CH2:2][CH2:3][CH2:4][CH3:5])[CH:24]=2)=[CH:16][C:15]=1[O:36][CH3:37])(=[O:12])=[O:11])[CH2:7][CH2:8][CH3:9]

Participants

Conditions

Temperature: 70 °C

Procedure

ml (0.95 mmol) of iodobutane is added to a solution of 400 mg (0.86 mmol) of methyl 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-hydroxyphenyl)propanoate (prepared according to Example 10i) and 178 mg (1.29 mmol) of potassium carbonate in 10 ml of methyl ethyl ketone, and the reaction mixture is then heated at 70° C. for 18 hours. The reaction is treated by adding 20 ml of water and then extracted with ethyl acetate. The organic phases are combined, dried over sodium sulfate, filtered and evaporated. The residue is purified by chromatography on a column of silica eluted with a 70/30 heptane/ethyl acetate mixture. 179 mg (40%) of methyl 3-(4-{3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propyl}-2-butoxyphenyl)propanoate are obtained in the form of a colorless oil.

Workup

additionThe reaction is treated
extractionextracted with ethyl acetate
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated
customThe residue is purified by chromatography on a column of silica
washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record: ord-7c657a361111472599c7b50ab9ed56c8
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879907B2

Reaction notes

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