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

HRID 898258Notes

Reaction equation

HRID 898258 reaction equation
C(=O)([O-])[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[NH:15][C:14](=[O:23])[C@@H:13]2[CH2:24][CH3:25])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([C@@H]1N(S(C2C=CC(O)=CC=2)(=O)=O)C2C(=CC=C(F)C=2)N(CCC)C1=O)C>>[CH2:28]([N:15]1[C:16]2[C:21](=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[N:12]([S:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)(=[O:11])=[O:10])[C@@H:13]([CH2:24][CH3:25])[C:14]1=[O:23])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 3

HCID 7498Benzyl BromideHCID 11538398(3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-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 11619070(3S)-1-benzyl-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one

Procedure

4-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate (see Example 20) was treated with benzyl bromide 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-benzyl-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-3,4-dihydroquinoxalin-2(1H)-one. [α]D25=−30° (c=0.0058 G/ML, DMSO); MS (ESI) m/z 441 ([M+H]+); MS (ESI) m/z 439 ([M−H]−); Anal. Calcd for C23H21FN2O4S: C, 62.71; H, 4.81; N, 6.36. Found: C, 62.23; H, 4.49; N, 6.23.

Sources & evidence

ORD record
ord-65bc3db6a50e44f7bb0efcb16d0f67c8
Source dataset
uspto-grants-2008_04
Patent number
US07351709B2

Reaction notes

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