3-Fluorophenol → HCID 66874849, compound

HRID 1799618Notes

Reaction equation

HRID 1799618 reaction equation
FC1C=C(O)C=CC=1.BrCCCCCCCCCO.[F:20][C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=1)[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34].FC1C=C(C=CC=1)OCCCCCCCCC(O)=O.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:33](=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:23]1[CH:35]=[CH:36][CH:37]=[C:21]([F:20])[CH:22]=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 97433-FluorophenolHCID 1087001-Nonanol, 9-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874069HCID 66874069, compoundHCID 66875184HCID 66875184, compound

Product 1

HCID 66874849HCID 66874849, compound

Procedure

The title compound, m/e=397.4 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, 3-fluorophenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(3-fluoro-phenoxy)-nonan-1-ol, which was oxidized in step 2 to 9-(3-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-(3-fluoro-phenoxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-2050993a7b3e457d87b8b22bd70311cb
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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