Isoxazolidine hydrochloride → 3-(4-Chloro-2-hydroxy-3-(isoxazolidin-2-ylsulfonyl)phenylamino)-4-ethoxycyclobut-3-ene-1,2-dione

HRID 2066031Notes

Reaction equation

HRID 2066031 reaction equation
[Cl:1][C:2]1[C:7]([S:8]([N:11]([O:14][CH3:15])[CH2:12][CH3:13])(=[O:10])=[O:9])=[C:6]([OH:16])[C:5]([NH:17][C:18]2[C:21](=[O:22])[C:20](=[O:23])[C:19]=2[O:24][CH2:25][CH3:26])=[CH:4][CH:3]=1.Cl.C(NOC)C.Cl.O1CCCN1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:17][C:18]2[C:21](=[O:22])[C:20](=[O:23])[C:19]=2[O:24][CH2:25][CH3:26])=[C:6]([OH:16])[C:7]=1[S:8]([N:11]1[CH2:12][CH2:13][CH2:15][O:14]1)(=[O:10])=[O:9]

Participants

4

Reactant 3

HCID 12304500Isoxazolidine hydrochlorideHCID 22613948Ethyl(methoxy)amine hydrochlorideHCID 866386316-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide

Product 1

HCID 866584043-(4-Chloro-2-hydroxy-3-(isoxazolidin-2-ylsulfonyl)phenylamino)-4-ethoxycyclobut-3-ene-1,2-dione

Procedure

This compound was prepared analogously to 6-chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide (Intermediate FA) by replacing N-ethyl-O-methylhydroxylamine hydrochloride (Intermediate G) with isoxazolidine hydrochloride. [M+H]+ 402.9

Sources & evidence

ORD record
ord-2c1bffbfc4d447d9bff50d470c175c44
Source dataset
uspto-grants-2012_10
Patent number
US08288588B2

Reaction notes

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