(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)ethanol → (S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)acetic acid

HRID 931797Notes

Reaction equation

HRID 931797 reaction equation
C(OC[C@@H](OC(C)(C)C)C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(N1CCOCC1)C=C2)(=[O:6])C(C)(C)C.[C:39]([O:43][C@@H:44]([C:47]1[C:48]([C:66]2[CH:71]=[CH:70][C:69]([Cl:72])=[CH:68][CH:67]=2)=[C:49]2[C:54](=[CH:55][C:56]=1[CH3:57])[N:53]=[C:52]([CH2:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH:51]=[CH:50]2)[CH2:45][OH:46])([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C@@H:44]([C:47]1[C:48]([C:66]2[CH:71]=[CH:70][C:69]([Cl:72])=[CH:68][CH:67]=2)=[C:49]2[C:54](=[CH:55][C:56]=1[CH3:57])[N:53]=[C:52]([CH2:58][CH2:59][C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1)[CH:51]=[CH:50]2)[C:45]([OH:6])=[O:46])([CH3:42])([CH3:40])[CH3:41]

Participants

3

Reactant 2

HCID 66631635(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)ethanolHCID 66631939HCID 66631939, compound

Product 1

HCID 56645258(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)acetic acid

Procedure

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)acetic acid (4.8 mg) was prepared in a similar manner as compound (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)acetic acid of Example 29 except using (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)ethanol instead of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol. 1H-NMR 400 MHz (CD3OD) δ 8.21 (d, J=8 Hz, 1 H), 7.93 (s, 1 H), 7.7-7.6 (m, 4 H), 7.37 (d, J=8 Hz, 1 H), 7.3-7.15 (m, 5 H), 5.24 (s, 1 H), 3.46 (d, J=7.6 Hz, 2 H), 3.18 (d, J=7.6 Hz, 2 H), 2.76 (s, 3 H), 0.96 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C30H31ClNO3: 488.2. Found: 488.2.

Sources & evidence

ORD record
ord-ab143304b4344e79a4f3f6dd4a3a5a5b
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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