(S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-cyclohexenyl-2,7-dimethylquinoline 1-oxide → (S)-Ethyl 2-(2-(acetoxymethyl)-5-cyclohexenyl-7-methylquinolin-6-yl)-2-tert-butoxyacetate

HRID 931779Notes

Reaction equation

HRID 931779 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([CH3:34])=[C:11]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]=2[C:16]2[CH:21]=[CH:20][C:19](Cl)=[CH:18][CH:17]=2)[N:7]=1)(=[O:3])[CH3:2].C(O[C@@H](C1C(C2CCCCC=2)=C2C(=CC=1C)[N+]([O-])=C(C)C=C2)C(OCC)=O)(C)(C)C.ClC1C=CC(C2C=C(C)C=C3C=2C=CC(C)=[N+]3[O-])=CC=1>>[C:1]([O:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][C:10]([CH3:34])=[C:11]([C@H:23]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:12]=2[C:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=2)[N:7]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 66631690(S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-cyclohexenyl-2,7-dimethylquinoline 1-oxideHCID 86691980(S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetateHCID 866919815-(4-Chlorophenyl)-2,7-dimethylquinoline 1-oxide

Product 1

HCID 68594582(S)-Ethyl 2-(2-(acetoxymethyl)-5-cyclohexenyl-7-methylquinolin-6-yl)-2-tert-butoxyacetate

Procedure

(S)-Ethyl 2-(2-(acetoxymethyl)-5-cyclohexenyl-7-methylquinolin-6-yl)-2-tert-butoxyacetate was prepared following the procedure used to prepare compound (S)-ethyl 2-(2-(acetoxymethyl)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetate of Example 16, except that (S)-6-(1-tert-butoxy-2-ethoxy-2-oxoethyl)-5-cyclohexenyl-2,7-dimethylquinoline 1-oxide was used instead of 2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-2,7-dimethylquinoline 1-oxide. LCMS-ESI+ (m/z): 454.3 (M+H)+.

Sources & evidence

ORD record
ord-03ebc554f083472894c03113d43fd37b
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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