4-Fluorophenol → HCID 66875165, compound

HRID 1799619Notes

Reaction equation

HRID 1799619 reaction equation
FC1C=CC(O)=CC=1.BrCCCCCCCCCO.[F:20][C:21]1[CH:37]=[CH:36][C:24]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])=[CH:23][CH:22]=1.FC1C=CC(OCCCCCCCCC(O)=O)=CC=1.Cl.Cl.[CH2:59]([O:66][C:67](=[O:75])[CH2:68][C@@H:69]([NH2:74])[CH2:70][N:71]([CH3:73])[CH3:72])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>>[CH2:59]([O:66][C:67](=[O:75])[CH2:68][C@@H:69]([NH:74][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:21]([F:20])=[CH:22][CH:23]=1)[CH2:70][N:71]([CH3:72])[CH3:73])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

6

Reactant 5

HCID 97324-FluorophenolHCID 1087001-Nonanol, 9-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 668751339-(4-Fluoro-phenoxy)-nonanoic acidHCID 689931199-(4-Fluoro-phenoxy)-nonan-1-ol

Product 1

HCID 66875165HCID 66875165, compound

Procedure

The title compound, m/e=395.5 ([M−H]−), was produced in analogy with example 18, steps 1 to 4. Thus, 4-fluorophenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(4-fluoro-phenoxy)-nonan-1-ol, which was oxidized in step 2 to 9-(4-fluoro-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-fluoro-phenoxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-b9380bc4c413412eb636507d94a5877e
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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