2-Tert-butoxy-2-[7-chloro-5-(4-chloro-phenyl)-2-methyl-quinolin-6-yl]ethanol → (S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2-ethyl-7-methylquinolin-6-yl)acetic acid

HRID 931786Notes

Reaction equation

HRID 931786 reaction equation
C([O:5]C(C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1Cl)N=C(C)C=C2)C(O)=O)(C)(C)C.[C:29]([O:33][C@@H:34]([C:37]1[C:38]([C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=2)=[C:39]2[C:44](=[CH:45][C:46]=1[CH3:47])[N:43]=[C:42]([CH2:48][CH3:49])[CH:41]=[CH:40]2)[CH2:35][OH:36])([CH3:32])([CH3:31])[CH3:30].C(OC(C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1Cl)N=C(C)C=C2)CO)(C)(C)C>>[C:29]([O:33][C@@H:34]([C:37]1[C:38]([C:50]2[CH:51]=[CH:52][C:53]([Cl:56])=[CH:54][CH:55]=2)=[C:39]2[C:44](=[CH:45][C:46]=1[CH3:47])[N:43]=[C:42]([CH2:48][CH3:49])[CH:41]=[CH:40]2)[C:35]([OH:5])=[O:36])([CH3:30])([CH3:31])[CH3:32]

Participants

4

Reactant 3

HCID 666314222-Tert-butoxy-2-[7-chloro-5-(4-chloro-phenyl)-2-methyl-quinolin-6-yl]ethanolHCID 66631622HCID 66631622, compoundHCID 66632060Tert-butoxy-[7-chloro-5-(4-chloro-phenyl)-2-methyl-quinolin-6-yl]-acetic acid

Product 1

HCID 66631560(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2-ethyl-7-methylquinolin-6-yl)acetic acid

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2-ethyl-7-methylquinolin-6-yl)acetic acid was prepared following the procedure used to prepare compound tert-butoxy-[7-chloro-5-(4-chloro-phenyl)-2-methyl-quinolin-6-yl]-acetic acid of Example 1, except that (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-ethyl-7-methylquinolin-6-yl)ethanol was used instead 2-tert-butoxy-2-[7-chloro-5-(4-chloro-phenyl)-2-methyl-quinolin-6-yl]ethanol. 1H-NMR 300 MHz, (CD3OD) δ 8.31 (d, 1H), 7.98 (s, 1H), 7.76 (d, 1H), 7.70-7.60 (m, 3H), 7.42-7.35 (m, 1H), 5.25 (s, 1H), 3.21 (q, 2H), 2.78 (s, 3H), 1.48 (t, 3H), 0.98 (s, 9H); LCMS-ESI+ (m/z): [M+H]+ calcd for C24H27ClNO3: 412.9. Found: 412.2, 414.2.

Sources & evidence

ORD record
ord-427a9cdcd7fb4f33aaff525436b714c7
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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