1-Nonanol, 9-bromo- → HCID 66874635, compound

HRID 1799623Notes

Reaction equation

HRID 1799623 reaction equation
FC1C(F)=C(F)C=CC=1O.BrCCCCCCCCCO.[F:22][C:23]1[C:39]([F:40])=[C:38]([F:41])[CH:37]=[CH:36][C:24]=1[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35].FC1C(F)=C(F)C=CC=1OCCCCCCCCC(O)=O.Cl.Cl.[CH2:65]([O:72][C:73](=[O:81])[CH2:74][C@@H:75]([NH2:80])[CH2:76][N:77]([CH3:79])[CH3:78])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>>[CH2:65]([O:72][C:73](=[O:81])[CH2:74][C@@H:75]([NH:80][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][O:25][C:24]1[CH:36]=[CH:37][C:38]([F:41])=[C:39]([F:40])[C:23]=1[F:22])[CH2:76][N:77]([CH3:78])[CH3:79])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Participants

6

Reactant 5

HCID 1087001-Nonanol, 9-bromo-HCID 1231742,3,4-TrifluorophenolHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874609HCID 66874609, compoundHCID 66875507HCID 66875507, compound

Product 1

HCID 66874635HCID 66874635, compound

Procedure

The title compound, m/e=433.5 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, 2,3,4-trifluorophenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(2,3,4-trifluoro-phenoxy)-nonan-1-ol, which was oxidized in step 2 to 9-(2,3,4-trifluoro-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-(2,3,4-trifluoro-phenoxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-73ff48d5a5094897bbead1cbc48602e9
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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