(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetic acid → (S)-6-(1-tert-Butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-7-methylquinoline-2-carboxylic acid

HRID 931769Notes

Reaction equation

HRID 931769 reaction equation
C([O:5][C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(CN(C)C)C=C2)C(O)=O)(C)(C)C.[C:32]([O:36][C@@H:37]([C:43]1[C:44]([C:56]2[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][CH:57]=2)=[C:45]2[C:50](=[CH:51][C:52]=1[CH3:53])[N:49]=[C:48]([CH2:54][OH:55])[CH:47]=[CH:46]2)[C:38]([O:40][CH2:41][CH3:42])=[O:39])([CH3:35])([CH3:34])[CH3:33]>>[C:32]([O:36][C@@H:37]([C:43]1[C:44]([C:56]2[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][CH:57]=2)=[C:45]2[C:50](=[CH:51][C:52]=1[CH3:53])[N:49]=[C:48]([C:54]([OH:5])=[O:55])[CH:47]=[CH:46]2)[C:38]([O:40][CH2:41][CH3:42])=[O:39])([CH3:33])([CH3:34])[CH3:35]

Participants

3

Reactant 2

HCID 56644427(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetic acidHCID 68587089(S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate

Product 1

HCID 66631131(S)-6-(1-tert-Butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-7-methylquinoline-2-carboxylic acid

Procedure

(S)-6-(1-tert-Butoxy-2-ethoxy-2-oxoethyl)-5-(4-chlorophenyl)-7-methylquinoline-2-carboxylic acid was prepared following the procedure used to prepare compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)acetic acid of Example 9, except that (S)-ethyl 2-tert-butoxy-2-(5-(4-chlorophenyl)-2-(hydroxymethyl)-7-methylquinolin-6-yl)acetate was used instead of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-2-((dimethylamino)methyl)-7-methylquinolin-6-yl)ethanol. LCMS-ESI+ (m/z): 456.2, 458.2 (M+H)+.

Sources & evidence

ORD record
ord-7a716a2b363f43fba7f5d8be71311ac2
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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