4-(Trifluoromethyl)phenol → HCID 66874314, compound

HRID 1799626Notes

Reaction equation

HRID 1799626 reaction equation
FC(F)(F)C1C=CC(O)=CC=1.BrCCCCCCCCCO.[F:23][C:24]([F:43])([F:42])[C:25]1[CH:41]=[CH:40][C:28]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])=[CH:27][CH:26]=1.FC(F)(F)C1C=CC(OCCCCCCCCC(O)=O)=CC=1.Cl.Cl.[CH2:68]([O:75][C:76](=[O:84])[CH2:77][C@@H:78]([NH2:83])[CH2:79][N:80]([CH3:82])[CH3:81])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>>[CH2:68]([O:75][C:76](=[O:84])[CH2:77][C@@H:78]([NH:83][C:38](=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][C:28]1[CH:40]=[CH:41][C:25]([C:24]([F:42])([F:43])[F:23])=[CH:26][CH:27]=1)[CH2:79][N:80]([CH3:81])[CH3:82])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

6

Reactant 5

HCID 678744-(Trifluoromethyl)phenolHCID 1087001-Nonanol, 9-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874953HCID 66874953, compoundHCID 66875648HCID 66875648, compound

Product 1

HCID 66874314HCID 66874314, compound

Procedure

The title compound, m/e=447.4 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, 4-trifluoromethyl-phenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(4-trifluoromethyl-phenoxy)-nonan-1-ol, which was oxidized in step 2 to 9-(4-trifluoromethyl-phenoxy)-nonanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-4-dimethylamino-3-[9-(4-trifluoromethyl-phenoxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-c43f9950857c47f491cee62fd7238964
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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