O-Cresol → tert-Butyl 3-((3-(1-(4-(o-tolyloxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)propanoate

HRID 2175285Notes

Reaction equation

HRID 2175285 reaction equation
ClC1C=C(Cl)C(Cl)=CC=1OCCCC(N1[C:19]2[C:14](=[C:15](C3C=NN(CC(OCC)=O)C=3)[CH:16]=[CH:17][CH:18]=2)[CH2:13]CC1)=O.OCCCC(N1C2C(=C(C3C=NN(CC(OCC)=O)C=3)C=CC=2)CCC1)=O.[OH:64][CH2:65][CH2:66][CH2:67][C:68]([N:70]1[C:79]2[C:74](=[C:75]([C:80]3[CH:81]=[C:82]([CH:97]=[CH:98][CH:99]=3)[CH2:83][O:84][C:85]([NH:87][CH2:88][CH2:89][C:90]([O:92][C:93]([CH3:96])([CH3:95])[CH3:94])=[O:91])=[O:86])[CH:76]=[CH:77][CH:78]=2)[CH2:73][CH2:72][CH2:71]1)=[O:69].ClC1C=C(Cl)C(Cl)=CC=1O.C1(C)C(O)=CC=CC=1>>[C:14]1([CH3:13])[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:64][CH2:65][CH2:66][CH2:67][C:68]([N:70]1[C:79]2[C:74](=[C:75]([C:80]3[CH:81]=[C:82]([CH:97]=[CH:98][CH:99]=3)[CH2:83][O:84][C:85]([NH:87][CH2:88][CH2:89][C:90]([O:92][C:93]([CH3:96])([CH3:94])[CH3:95])=[O:91])=[O:86])[CH:76]=[CH:77][CH:78]=2)[CH2:73][CH2:72][CH2:71]1)=[O:69]

Participants

6

Reactant 5

HCID 335O-CresolHCID 72712,4,5-TrichlorophenolHCID 70982571tert-Butyl 3-((3-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)propanoateHCID 70982627Ethyl 2-(4-(1-(4-(2,4,5-trichlorophenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetateHCID 70983434Ethyl 2-(4-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetate

Product 1

HCID 70982731tert-Butyl 3-((3-(1-(4-(o-tolyloxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)propanoate

Procedure

The title compound was prepared using a procedure analogous to ethyl 2-(4-(1-(4-(2,4,5-trichlorophenoxy)butanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetate except that ethyl 2-(4-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)-1H-pyrazol-1-yl)acetate was replaced with tert-butyl 3-((3-(1-(4-hydroxybutanoyl)-1,2,3,4-tetrahydroquinolin-5-yl)benzyloxy)carbonylamino)propanoate and 2,4,5-trichlorophenol was replaced with o-cresol. LCMS, [M+H]+=587.3.

Sources & evidence

ORD record
ord-4132530ba8f64a50819f9d8a30e02f30
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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