Methanesulfonyl chloride → HCID 86625774, compound

HRID 1821138Notes

Reaction equation

[CH3:1][C:2]1[CH:12]=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[S:25][C:24]([CH3:26])=[C:23]4[C:19]=3[CH2:20][C@H:21]3[C:27]([CH3:29])([CH3:28])[C@H:22]34)[O:15][N:14]=2)[CH:10]=[C:9]([CH3:30])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][OH:8].CCN(C(C)C)C(C)C.[CH3:40][S:41](Cl)(=[O:43])=[O:42]>C(Cl)Cl>[CH3:1][C:2]1[CH:12]=[C:11]([C:13]2[N:17]=[C:16]([C:18]3[S:25][C:24]([CH3:26])=[C:23]4[C:19]=3[CH2:20][C@H:21]3[C:27]([CH3:28])([CH3:29])[C@H:22]34)[O:15][N:14]=2)[CH:10]=[C:9]([CH3:30])[C:3]=1[O:4][CH2:5][CH2:6][CH2:7][O:8][S:41]([CH3:40])(=[O:43])=[O:42]

Participants

Conditions

Temperature: 0 °C

Procedure

At 0° C., a solution of 3-{2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxy}-propan-1-ol (170 mg, 0.40 mmol) and DIPEA (0.11 mL, 0.64 mmol) in DCM (5 mL) is treated with methanesulfonyl chloride (0.04 mL, 0.48 mmol). The reaction mixture is stirred at 0° C. for 30 min, then at rt for 1 h before it is diluted with DCM (15 mL) and washed with 0.1 N aq. NaOH (20 mL) followed by 10% aq. citric acid solution (20 mL). The organic layer is dried over Na2SO4 and evaporated to dryness to give methanesulfonic acid 3-{2,6-dimethyl-4-[5-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-[1,2,4]oxadiazol-3-yl]-phenoxy}-propyl ester (185 mg) as a beige resin; LC-MS: tR=1.23 min, [M+1]+=503.20.

Workup

washwashed with 0.1 N aq. NaOH (20 mL)
dry with materialThe organic layer is dried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-ae767683baea41fe9c5183c8665e6cae
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07605269B2

Reaction notes

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