Iodoethane → (3S)-1-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3-methyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898255Notes

Reaction equation

HRID 898255 reaction equation
C(=O)(OC1C=CC(S(N2C3C(=CC=C(F)C=3)NC(=O)[C@@H]2C)(=O)=O)=CC=1)OCC.ICC.[CH2:32]([C@@H:34]1[N:43]([S:44]([C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[C:42]2[C:37](=[CH:38][CH:39]=[C:40]([F:54])[CH:41]=2)[N:36]([CH2:55][CH2:56]C)[C:35]1=[O:58])C>>[CH2:55]([N:36]1[C:37]2[C:42](=[CH:41][C:40]([F:54])=[CH:39][CH:38]=2)[N:43]([S:44]([C:47]2[CH:52]=[CH:51][C:50]([OH:53])=[CH:49][CH:48]=2)(=[O:46])=[O:45])[C@@H:34]([CH3:32])[C:35]1=[O:58])[CH3:56]

Participants

4

Reactant 3

HCID 6340IodoethaneHCID 11538398(3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-oneHCID 69222681ethyl 4-{[(2S)-7-fluoro-2-methyl-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

Product 1

HCID 11682079(3S)-1-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3-methyl-3,4-dihydroquinoxalin-2(1H)-one

Procedure

Ethyl 4-{[(2S)-7-fluoro-2-methyl-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate was treated with iodoethane according to the procedure for the preparation of (3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-one (see Example 20) to yield (3S)-1-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3-methyl-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−67° (c=0.005 G/ML, DMSO); MS (ESI) m/z 365 ([M+H]+); MS (ESI) m/z 363 ([M−H]−); Anal. Calcd for C17H17FN2O4S: C, 56.03; H, 4.70; N, 7.69. Found: C, 54.80; H, 4.47; N, 7.39.

Sources & evidence

ORD record
ord-dcfbaa2ab21c448f8ce4d28f259360fa
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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