Water → HCID 18007941, compound

HRID 429781Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][CH:14]=[C:15]2[CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])=[CH:10][CH:9]=1.C(N(CC)CC)C.[S:31](Cl)([CH3:34])(=[O:33])=[O:32].O>ClCCl>[CH3:34][S:31]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]2[C:16](=[C:15]([CH2:18][CH2:19][NH:20][C:21](=[O:23])[CH3:22])[CH:14]=[CH:13][CH:12]=2)[CH:17]=1)(=[O:33])=[O:32]

Participants

Conditions

Temperature: 0 °C

Procedure

In a 250 ml round-bottomed flask, dissolve the compound obtained in Step B (3.15 g, 10 mmol) in 50 ml of dichloromethane and add triethylamine (1.6 ml; 12 mmol). Cool in an ice/salt bath at 0° C, and then add mesyl chloride (0.93 ml; 12 mmol) dropwise with stirring using a magnetic stirrer. Allow the reaction mixture to return to room temperature and stir for 5 hours. Add 100 ml of water and extract the aqueous phase 3 times with dichloromethane. Wash the organic phase with 3×20 ml of an aqueous 1M hydrochloric acid solution and then with water, dry over magnesium sulphate and evaporate under reduced pressure. Purify the resulting oil by chromatography over silica gel (eluant: acetone/cyclohexane (3/7)). Colourless oil.

Workup

customto return to room temperature
extractionextract the aqueous phase 3 times with dichloromethane
washWash the organic phase with 3×20 ml of an aqueous 1M hydrochloric acid solution
dry with materialwith water, dry over magnesium sulphate
customevaporate under reduced pressure
customPurify the resulting oil by chromatography over silica gel (eluant: acetone/cyclohexane (3/7))

Sources & evidence

ORD record: ord-c03b94c69de246438579c137b8637c93
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06319930B1

Reaction notes

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