(S)-6-(1-tert-Butoxy-2-(pivaloyloxy)ethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide → (S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methyl(phenyl)amino)methyl)quinolin-6-yl)ethyl pivalate
Reaction equation
[C:1]([O:5][C@@H:6]([C:12]1[C:13]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[N:18]=[C:17]([CH2:23][N:24]([CH3:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:16]=[CH:15]2)[C:7](OCC)=[O:8])([CH3:4])([CH3:3])[CH3:2].C(O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)[N+]([O-])=C(C)C=C2)C[O:46][C:47](=O)[C:48]([CH3:51])([CH3:50])[CH3:49])(C)(C)C>>[C:47]([O:8][CH2:7][C@@H:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C:12]1[C:13]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[C:14]2[C:19](=[CH:20][C:21]=1[CH3:22])[N:18]=[C:17]([CH2:23][N:24]([CH3:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH:16]=[CH:15]2)(=[O:46])[C:48]([CH3:51])([CH3:50])[CH3:49]Participants
3
Reactant 2
Product 1
Procedure
(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methyl(phenyl)amino)methyl)quinolin-6-yl)ethyl pivalate was prepared following the procedure used to prepare compound (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-((methyl(phenyl)amino)methyl)quinolin-6-yl)acetate of Example 14, except that (S)-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide was used instead of (S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide. LCMS-ESI+ (m/z): 573.3, 575.4 (M+H)+.
Sources & evidence
- ORD record
- ord-c65a1517c1604f429e9abb7156fac43b
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296758B2
Reaction notes
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