Sodium Chloride → HCID 86642709, compound

HRID 1361080Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([S:10](Cl)(=[O:12])=[O:11])[CH3:9].[CH2:14]([O:18][C:19]1[CH:20]=[C:21]([CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:22]=[CH:23][C:24]=1[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([O:35][CH3:36])[CH:29]=1)[CH2:15][CH2:16][CH3:17].[Cl-].[Na+]>ClCCl>[CH2:14]([O:18][C:19]1[CH:20]=[C:21]([CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:22]=[CH:23][C:24]=1[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][S:10]([CH2:8][CH3:9])(=[O:12])=[O:11])=[C:30]([O:35][CH3:36])[CH:29]=1)[CH2:15][CH2:16][CH3:17]

Participants

Conditions

Temperature: -20 °C

Procedure

0.2 ml (1.6 mmol) of triethylamine and then 0.15 ml (1.7 mmol) of ethanesulfonyl chloride are added to a solution of 0.5 g (1.25 mmol) of methyl 3-{3-butoxy-4-[3-(4-hydroxy-3-methoxyphenyl)propyl]phenyl}propanoate (prepared according to Example 1d) in 3 ml of dichloromethane, cooled beforehand to −20° C. The reaction medium is stirred at room temperature for 3 hours and is then treated by addition of saturated aqueous sodium chloride solution and 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 90/10 heptane/ethyl acetate mixture. 618 mg (99%) of methyl 3-{3-butoxy-4-[3-(4-ethanesulfonyloxy-3-methoxyphenyl)propyl]phenyl}propanoate are obtained in the form of a colorless oil.

Workup

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 90/10 heptane/ethyl acetate mixture

Sources & evidence

ORD record: ord-ccd5f56d700f4454ac335cc66b7e1d1f
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879907B2

Reaction notes

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