Methyl iodide → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-methoxy-7-methylquinolin-6-yl)acetic acid
Reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][C:13]([CH3:35])=[C:14]([C@H:26]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[C:27]([OH:29])=[O:28])[C:15]=2[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[N:10]=1)C1C=CC=CC=1.IC>>[C:31]([O:30][C@@H:26]([C:14]1[C:15]([C:19]2[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=2)=[C:16]2[C:11](=[CH:12][C:13]=1[CH3:35])[N:10]=[C:9]([O:8][CH3:1])[CH:18]=[CH:17]2)[C:27]([OH:29])=[O:28])([CH3:34])([CH3:32])[CH3:33]Participants
3
Procedure
(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2-methoxy-7-methylquinolin-6-yl)acetic acid (66) (2.3 mg) was prepared in a similar manner as compound (S)-2-(2-(benzyloxy)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetic acid of Example 65 except using iodomethane instead of benzyl bromide. 1H-NMR 400 MHz (CD3OD) δ 7.68 (s, 1 H), 7.6-7.5 (m, 4 H), 7.30 (d, J=8 Hz, 1 H), 6.87 (d, J=9.6 Hz, 1H), 5.16 (s, 1 H), 4.08 (s, 3 H), 2.62 (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-3f1370c440734abea81bf1a4f493a530
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296758B2
Reaction notes
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