(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol → (S)-2-(2-(Benzyloxy)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetic acid

HRID 931810Notes

Reaction equation

HRID 931810 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]([O:46][C:47]1[CH:56]=[CH:55][C:54]2[C:49](=[CH:50][C:51]([CH3:72])=[C:52]([C@H:64]([O:67][C:68]([CH3:71])([CH3:70])[CH3:69])[CH2:65][OH:66])[C:53]=2[C:57]2[CH:62]=[CH:61][C:60]([Cl:63])=[CH:59][CH:58]=2)[N:48]=1)[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]([O:46][C:47]1[CH:56]=[CH:55][C:54]2[C:49](=[CH:50][C:51]([CH3:72])=[C:52]([C@H:64]([O:67][C:68]([CH3:69])([CH3:71])[CH3:70])[C:65]([OH:6])=[O:66])[C:53]=2[C:57]2[CH:62]=[CH:61][C:60]([Cl:63])=[CH:59][CH:58]=2)[N:48]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 3

HCID 66630867(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanolHCID 66631276(S)-2-(2-(benzyloxy)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyethanolHCID 66631939HCID 66631939, compound

Product 1

HCID 66631303(S)-2-(2-(Benzyloxy)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetic acid

Procedure

(S)-2-(2-(Benzyloxy)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyacetic acid (65A) (3.3 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-(2-(benzyloxy)-5-(4-chlorophenyl)-7-methylquinolin-6-yl)-2-tert-butoxyethanol instead of ((S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-morpholinoquinolin-6-yl)ethanol. 1H-NMR 400 MHz (CD3OD) δ 7.82 (d, J=9.6 Hz, 1 H), 7.71 (s, 1 H), 7.80 (m, 3 H), 7.51 (m, 2 H), 7.41-7.10 (m, 4 H), 7.12 (d, J=9.6 Hz, 1 H), 5.58 (s, 2 H), 5.18 (s, 1 H), 2.66 (s, 3 H), 0.97 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C29H29ClNO4: 490.2. Found: 490.2.

Sources & evidence

ORD record
ord-2204bf6bd6514823a3ad78074210899e
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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