Methanesulfonyl chloride → HCID 57508923, compound

HRID 1665965Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH2:15][CH2:16][C:17]([C:19]2[S:20][C:21]([CH3:30])=[C:22]3[CH2:27][C:26]([CH3:29])([CH3:28])[CH2:25][CH2:24][C:23]=23)=[O:18])[CH:5]=[C:6]([O:13][CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][OH:12].CCN(C(C)C)C(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:15][CH2:16][C:17](=[O:18])[C:19]2[S:20][C:21]([CH3:30])=[C:22]3[CH2:27][C:26]([CH3:28])([CH3:29])[CH2:25][CH2:24][C:23]=23)[CH:5]=[C:6]([O:13][CH3:14])[C:7]=1[O:8][CH2:9][CH2:10][CH2:11][O:12][S:41]([CH3:40])(=[O:43])=[O:42]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-[3-chloro-4-(3-hydroxy-propoxy)-5-methoxy-phenyl]-1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propan-1-one (170 mg, 0.38 mmol) in DCM (10 mL) and DIPEA (0.10 mL, 0.60 mmol) is added methane sulfonylchloride (0.04 mL, 0.45 mmol) at 0° C. The reaction mixture is stirred at 0° C. for 30 min. Another portion of methane sulfonylchloride (0.04 mL, 0.45 mmol) is added and stirring is continued for 20 min. The reaction mixture is diluted with DCM, washed with 0.1 N aq. NaOH followed by 10% aq. citric acid solution, dried over MgSO4 and evaporated to give methanesulfonic acid 3-{2-chloro-6-methoxy-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propyl]-phenoxy}-propyl ester (196 mg) as a yellow oil; LC-MS: tR=1.17 min, [M+1]+=529.17.

Workup

stirringstirring
waitis continued for 20 min
washwashed with 0.1 N aq. NaOH
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-a13e6fbf93a04314bdaeda270a098755
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08039644B2

Reaction notes

Loading…