(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol → (S)-2-(1-Benzyl-5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyacetic acid

HRID 931811Notes

Reaction equation

HRID 931811 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.[CH2:39]([N:46]1[C:55]2[C:50](=[C:51]([C:65]3[CH:70]=[CH:69][C:68]([Cl:71])=[CH:67][CH:66]=3)[C:52]([C@H:57]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])[CH2:58][OH:59])=[C:53]([CH3:56])[CH:54]=2)[CH:49]=[CH:48][C:47]1=[O:72])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(O[C@@H](C1C(C2C=CC(Cl)=CC=2)=C2C(=CC=1C)N=C(N1CCOCC1)C=C2)CO)(C)(C)C>>[CH2:39]([N:46]1[C:55]2[C:50](=[C:51]([C:65]3[CH:70]=[CH:69][C:68]([Cl:71])=[CH:67][CH:66]=3)[C:52]([C@H:57]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])[C:58]([OH:6])=[O:59])=[C:53]([CH3:56])[CH:54]=2)[CH:49]=[CH:48][C:47]1=[O:72])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

4

Reactant 3

HCID 66630867(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanolHCID 66631939HCID 66631939, compoundHCID 66633870(S)-1-benzyl-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-one

Product 1

HCID 68585647(S)-2-(1-Benzyl-5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyacetic acid

Procedure

(S)-2-(1-Benzyl-5-(4-chlorophenyl)-7-methyl-2-oxo-1,2-dihydroquinolin-6-yl)-2-tert-butoxyacetic acid (65B) (5.4 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)-1-benzyl-6-(1-tert-butoxy-2-hydroxyethyl)-5-(4-chlorophenyl)-7-methylquinolin-2(1H)-one instead of ((S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol. 1H-NMR 400 MHz (CD3OD) δ 7.6-7.5 (m, 3 H), 7.4-7.2 (m, 8 H), 6.59 (d, J=9.6 Hz, 1 H), 5.64 (s, 2 H), 5.02 (s, 1 H), 2.47 (s, 3 H), 0.94 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C29H29ClNO4: 490.2. Found: 490.2; LCMS-ESI+ (m/z): [M+H]+ calcd for C29H27ClNO4: 488.2. Found: 488.0.

Sources & evidence

ORD record
ord-67716b74ea324772aa66739ac5f9d8a1
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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