Water → HCID 178505292, compound

HRID 1243640Notes

Reaction equation

[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[Cl:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([C@@H:17]2[CH2:22][O:21][C@@H:20]([CH2:23][CH2:24][CH2:25][OH:26])[O:19][CH2:18]2)=[CH:9][CH:8]=1.C(N(CC)CC)C.O>ClCCl>[CH3:4][S:1]([O:26][CH2:25][CH2:24][CH2:23][C@H:20]1[O:21][CH2:22][C@H:17]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]([Cl:6])=[CH:8][CH:9]=2)[CH2:18][O:19]1)(=[O:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 0.256 g (2.23 mmol) of mesyl chloride in 2 ml of dichloromethane is added, dropwise, to a solution of 0.530 g (1.72 mmol) of trans-3-[5-(4-chloronaphthalen-1-yl)-1,3-dioxan-2-yl]-1-propanol prepared in step 5.1 and of 0.48 ml (3.45 mmol) of triethylamine in 8 ml of dichloromethane cooled to 0° C. under an inert atmosphere. The reaction mixture is stirred at 0° C. for 1 hour. 25 ml of water and 50 ml of dichloromethane are added. The mixture is separated off after settling out and the aqueous phase is extracted with 50 ml of dichloromethane. The organic phases are washed with 25 ml of a saturated aqueous sodium chloride solution, drying is carried out over magnesium sulfate and concentration is carried out under vacuum, to obtain 0.66 g of product in the form of a white solid used without modification in the following step.

Workup

customThe mixture is separated off
extractionthe aqueous phase is extracted with 50 ml of dichloromethane
washThe organic phases are washed with 25 ml of a saturated aqueous sodium chloride solution
customdrying
concentrationis carried out over magnesium sulfate and concentration

Sources & evidence

ORD record: ord-f77584c999f3450ab960f42b298a717d
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07119116B2

Reaction notes

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