Methanesulfonyl chloride → (5RS)-3-(3-Fluoro-4-iodophenyl)-5-methanesulfonyloxymethyl-4,5-dihydro-isoxazole

HRID 1793677Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][OH:15])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[I:8].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][CH:12]([CH2:14][O:15][S:17]([CH3:16])(=[O:19])=[O:18])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[I:8]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 22022995(5RS)-3-(3-Fluoro4-iodophenyl)-5-hydroxymethyl-4,5-dihydroisoxazole

Product 1

HCID 22022974(5RS)-3-(3-Fluoro-4-iodophenyl)-5-methanesulfonyloxymethyl-4,5-dihydro-isoxazole

Procedure

(5RS)-3-(3-Fluoro-4-iodophenyl)-5-hydroxymethyl-4,5-dihydroisoxazole (2 g, 6.2 mM) was treated with methanesulfonyl chloride under essentially the conditions of the equivalent intermediate of Example 4. Product was obtained as a white solid (2.18 g) without chromatography. MS (EI): 399 (M+) for C11H11FINO4S

Sources & evidence

ORD record: ord-c4b2a98cb5fb456aba204d56b97b859e
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07081538B1

Reaction notes

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