(3R)-3-Ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one → (3S)-3-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one

HRID 898264Notes

Reaction equation

HRID 898264 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@@H:9]([CH2:13][CH3:14])[C:10](O)=[O:11])=[C:4]([N+:15]([O-])=O)[CH:3]=1.C([C@H]1NC2C(=CC(F)=CC=2)NC1=O)C>>[CH2:13]([C@@H:9]1[NH:8][C:5]2[C:4](=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[NH:15][C:10]1=[O:11])[CH3:14]

Participants

3

Reactant 2

HCID 69220784(3R)-3-Ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-oneHCID 69222707(2S)-2-[(4-fluoro-2-nitrophenyl)amino]butanoic acid

Product 1

HCID 69221470(3S)-3-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one

Procedure

(2S)-2-[(4-Fluoro-2-nitrophenyl)amino]butanoic acid was treated according to the procedure for the preparation of (3R)-3-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one (see Example 1) to yield (3S)-3-ethyl-7-fluoro-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=+33.42° (c=0.01 G/ML, DMSO); MS (ESI) m/z 195 ([M+H]+); Anal. Calcd for C10H11FN2O: C, 61.85; H, 5.71; N, 14.42. Found: C, 61.84; H, 5.72; N, 14.24.

Sources & evidence

ORD record
ord-88374db718af4adb8260dd7663658346
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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