Methanesulfonyl chloride → HCID 86622510, compound

HRID 2261449Notes

Reaction equation

[OH:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH2:12][CH2:13][C:14]([C:16]2[S:23][C:22]([CH3:24])=[C:21]3[C:17]=2[CH2:18][C@H:19]2[C:25]([CH3:27])([CH3:26])[C@H:20]23)=[O:15])=[CH:7][C:6]=1[CH3:28].CCN(C(C)C)C(C)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[CH3:28][C:6]1[CH:7]=[C:8]([CH2:12][CH2:13][C:14](=[O:15])[C:16]2[S:23][C:22]([CH3:24])=[C:21]3[C:17]=2[CH2:18][C@H:19]2[C:25]([CH3:26])([CH3:27])[C@H:20]23)[CH:9]=[C:10]([CH3:11])[C:5]=1[O:4][CH2:3][CH2:2][O:1][S:39]([CH3:38])(=[O:41])=[O:40]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one (1.55 g, 3.89 mmol) in DCM (60 mL) and DIPEA (1.07 mL, 6.22 mmol) is added methane sulfonylchloride (0.362 mL, 4.67 mmol) at 0° C. The reaction mixture is stirred at 0° C. for 30 min. Another portion of methane sulfonylchloride (0.362 mL, 4.67 mmol) is added and stirring is continued for 30 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 2-{2,6-dimethyl-4-[3-oxo-3-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propyl]-phenoxy}-ethyl ester (1.57 g) as an orange resin; LC-MS: tR=1.14 min, [M+1]+=477.35; 1H NMR (CDCl3): δ 6.86 (s, 2H), 4.57-4.50 (m, 2H), 4.05-4.00 (m, 2H), 3.10 8s, 3H), 3.03-2.85 (m, 5H), 2.79 (d, J=18.8 Hz, 1H), 2.37 8s, 3H), 2.25 (s, 6H), 1.92-1.85 (m, 2H), 1.11 (s, 3H), 0.70 (s, 3H).

Workup

stirringstirring
waitis continued for 30 min
washwashed with 0.1 N aq. NaOH
dry with materialdried over MgSO4
customevaporated

Sources & evidence

ORD record: ord-1b4b2dc227614eabb4005c22d5f40ec7
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846964B2

Reaction notes

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