Ethyl(methoxy)amine hydrochloride → 3-[4-chloro-2-hydroxy-3-((S)-4-hydroxy-isoxazolidine-2-sulfonyl)-phenylamino]-4-ethoxy-cyclobut-3-ene-1,2-dione

HRID 1669617Notes

Reaction equation

HRID 1669617 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(N[O:31]C)C.[O:33]1[CH2:37][C@@H:36]([OH:38])[CH2:35][NH:34]1.O1C[C@H](O)CN1>>[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][C@H:13]([OH:31])[CH2:15][O:14]1)(=[O:10])=[O:9].[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:34]1[CH2:35][C@@H:36]([OH:38])[CH2:37][O:33]1)(=[O:10])=[O:9]

Participants

6

Reactant 4

HCID 22613948Ethyl(methoxy)amine hydrochlorideHCID 40429112(R)-isoxazolidin-4-ol2×HCID 40531170(S)-isoxazolidin-4-ol2×HCID 866386316-Chloro-3-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-2-hydroxy-N-methoxy-N-ethyl-benzenesulfonamide

Product 2

HCID 866386373-[4-chloro-2-hydroxy-3-((S)-4-hydroxy-isoxazolidine-2-sulfonyl)-phenylamino]-4-ethoxy-cyclobut-3-ene-1,2-dioneHCID 866386383-[4-chloro-2-hydroxy-3-((R)-4-hydroxy-isoxazolidine-2-sulfonyl)-phenylamino]-4-ethoxy-cyclobut-3-ene-1,2-dione

Procedure

These compounds namely, 3-[4-chloro-2-hydroxy-3-((S)-4-hydroxy-isoxazolidine-2-sulfonyl)-phenylamino]-4-ethoxy-cyclobut-3-ene-1,2-dione (Intermediate FC) and 3-[4-chloro-2-hydroxy-3-((R)-4-hydroxy-isoxazolidine-2-sulfonyl)-phenylamino]-4-ethoxy-cyclobut-3-ene-1,2-dione (Intermediate FD) are 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 hydrochloride salts of either (S)-isoxazolidin-4-ol (Intermediate I) or (R)-isoxazolidin-4-ol (Intermediate J). [M+H]+ 418.9 and [M+H]+ 418.9.

Sources & evidence

ORD record
ord-f93df2522d1a4fbe8dd708810ac102ff
Source dataset
uspto-grants-2011_08
Patent number
US07989497B2

Reaction notes

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