(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)ethyl pivalate → (S)-6-(1-tert-Butoxy-2-(pivaloyloxy)ethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide

HRID 931755Notes

Reaction equation

HRID 931755 reaction equation
Br[C:2]1[C:11]([C@H:12]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])=[C:10]([CH3:26])[CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:28])=[N+:7]2[O-:27].C(OC[C@@H](OC(C)(C)C)C1C([C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=2)=C2C(=CC=1C)N=C(C)C=C2)(=O)C(C)(C)C>>[C:22]([O:21][C@@H:12]([C:11]1[C:2]([C:50]2[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=2)=[C:3]2[C:8](=[CH:9][C:10]=1[CH3:26])[N+:7]([O-:27])=[C:6]([CH3:28])[CH:5]=[CH:4]2)[CH2:13][O:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:25])([CH3:24])[CH3:23]

Participants

3

Reactant 2

HCID 66631480(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)ethyl pivalateHCID 66631609(S)-5-bromo-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-2,7-dimethylquinoline 1-oxide

Product 1

HCID 66631094(S)-6-(1-tert-Butoxy-2-(pivaloyloxy)ethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide

Procedure

Following the procedure used to prepare compound (S)-5-bromo-6-(1-tert-butoxy-2-(pivaloyloxy)ethyl)-2,7-dimethylquinoline 1-oxide of Example 9, except that (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)ethyl pivalate was used instead of (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate. LCMS-ESI+ (m/z): 484.3, 486.3 (M+H)+.

Sources & evidence

ORD record
ord-ee662c8493724d59ad30a1c269c9b5bc
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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