(S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)acetic acid → (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)acetic acid

HRID 931705Notes

Reaction equation

HRID 931705 reaction equation
[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)=[C:12]2[C:17](=[CH:18][C:19]=1Cl)[N:16]=[C:15]([CH3:21])[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2].[C:29](O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(C)C=C2)CO)(C)(C)C>>[C:1]([O:5][C@@H:6]([C:10]1[C:11]([C:22]2[CH:23]=[CH:24][C:25]([Cl:28])=[CH:26][CH:27]=2)=[C:12]2[C:17](=[CH:18][C:19]=1[CH3:29])[N:16]=[C:15]([CH3:21])[CH:14]=[CH:13]2)[C:7]([OH:9])=[O:8])([CH3:2])([CH3:4])[CH3:3]

Participants

3

Reactant 2

HCID 56644218(S)-2-tert-butoxy-2-(7-chloro-5-(4-chlorophenyl)-2-methylquinolin-6-yl)acetic acidHCID 66631683(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)ethanol

Product 1

HCID 56644219(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)acetic acid

Procedure

(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)acetic acid (2K) was prepared following the procedure used to prepare compound 1L of Example 1, except that (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)ethanol (2J) was used instead of compound 1K. 1H-NMR 300 MHz, (CD3OD) δ 8.31 (d, 1H), 7.97 (s, 1H), 7.73 (d, 1H), 7.70-7.60 (m, 3H), 7.42-7.38 (m, 1H), 5.25 (s, 1H), 2.96 (s, 3H), 2.78 (s, 3H), 0.98 (s, 9H); LCMS-ESI+ (m/z): [M+H]+ calcd for C23H25ClNO3: 398.9. Found: 398.2, 400.1.

Sources & evidence

ORD record
ord-3da34f7174564f0b898381b197a2c1fd
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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