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

HRID 931796Notes

Reaction equation

HRID 931796 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]([C:58]#[C: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].[H][H]>C(O)C.[Rh]>[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]([C:58]#[C: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].[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])([CH3:40])[CH3:41]

Participants

7

Reactant 3

HCID 66631316(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)ethanol2×HCID 66631939HCID 66631939, compoundHCID 178418361HCID 178418361, compound

Product 2

HCID 56645057(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)acetic acidHCID 66631635(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)ethanol

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 702EthanolSolvent

Procedure

Preparation of(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)acetic acid (37A): (S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)acetic acid (4.9 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-(phenylethynyl)quinolin-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 7.95 (m, 1 H), 7.90 (s, 1 H), 7.7-7.6 (m, 6 H), 7.50 (m, 3 H), 7.37 (d, J=8.8 Hz, 1 H), 5.23 (s, 1 H), 2.72 (s, 3 H), 0.99 (s, 9 H); LCMS-ESI+ (m/z): [M+H]+ calcd for C30H27ClNO3: 484.2. Found: 484.2. Preparation of(S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)ethanol: The mixture of (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(phenylethynyl)quinolin-6-yl)ethanol (6 mg) and rhodium on alumina (2 mg) in ethanol (1.5 mL) was stirred under 1 atm of hydrogen for 3 hours. Celite was added, and the mixture was filtered and washed with ethyl acetate. Concentration of the mother liquor under reduced pressure gave (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-phenethylquinolin-6-yl)ethanol (6.5 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C30H33ClNO2: 474.2. Found: 474.3.

Workup

  1. additionCelite was added
  2. filtrationthe mixture was filtered
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-1f62cd2e58124d8c98c49453635fb130
Source dataset
uspto-grants-2016_03
Patent number
US09296758B2

Reaction notes

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