(S)-6-Fluoro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one → ethyl 4-{[(2S)-7-fluoro-2-methyl-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

HRID 898254Notes

Reaction equation

HRID 898254 reaction equation
F[C:2]1C=C2C(=C[CH:11]=1)NC(=O)[C@H](C)N2.[C:14](=[O:40])([O-:39])[O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([F:35])[CH:33]=3)[NH:28][C:27](=[O:36])[C@@H:26]2[CH2:37]C)(=[O:24])=[O:23])=[CH:18][CH:17]=1>>[C:14](=[O:40])([O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([N:25]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([F:35])[CH:33]=3)[NH:28][C:27](=[O:36])[C@@H:26]2[CH3:37])(=[O:24])=[O:23])=[CH:18][CH:17]=1)[O:39][CH2:2][CH3:11]

Participants

3

Reactant 2

HCID 69221304(S)-6-Fluoro-3-methyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 866027294-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

Product 1

HCID 69222681ethyl 4-{[(2S)-7-fluoro-2-methyl-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

Procedure

(3S)-6-Fluoro-3-methyl-3,4-dihydroquinoxalin-2(1H)-one was treated according to the procedure for the preparation of 4-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate (see Example 20) to yield ethyl 4-{[(2S)-7-fluoro-2-methyl-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate. MS (ESI) m/z 409 ([M+H]+); MS (ESI) m/z 407 ([M−H]−);

Sources & evidence

ORD record
ord-503e93d4f9e84acda9fe2713e98f584d
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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