Methyl iodide → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-1,7-dimethyl-2-oxo-1,2-dihydroquinolin-6-yl)acetic acid
Reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[C:13]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)[C:14]([C@H:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:20]([OH:22])=[O:21])=[C:15]([CH3:18])[CH:16]=2)[CH:11]=[CH:10][C:9]1=[O:35])C1C=CC=CC=1.IC>>[C:24]([O:23][C@@H:19]([C:14]1[C:13]([C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[C:12]2[C:17](=[CH:16][C:15]=1[CH3:18])[N:8]([CH3:1])[C:9](=[O:35])[CH:10]=[CH:11]2)[C:20]([OH:22])=[O:21])([CH3:27])([CH3:25])[CH3:26]Participants
3
Procedure
(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-1,7-dimethyl-2-oxo-1,2-dihydroquinolin-6-yl)acetic acid (67) (2.0 mg) was prepared in a similar manner as compound (S)-2-(1-benzyl-5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyacetic acid of Example 65 except using iodomethane instead of benzyl bromide. 1H-NMR 400 MHz (CD3OD) δ 7.6-7.5 (m, 4 H), 7.3-7.26 (m, 2 H), 6.49 (d, J=10 Hz, 1 H), 5.06 (s, 1 H), 3.78 (s, 3 H), 2.64 (s, 3 H), 0.97 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C23H25ClNO4: 414.1. Found: 414.2; LCMS-ESI− (m/z): [M−H]− calcd for C23H23ClNO4: 412.1. Found: 412.0.
Sources & evidence
- ORD record
- ord-92a3b90c827f4a55988dc3a7dda6c126
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296758B2
Reaction notes
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