3,4-Difluorophenol → HCID 66875043, compound

HRID 1799622Notes

Reaction equation

HRID 1799622 reaction equation
FC1C=C(O)C=CC=1F.BrCCCCCCCCCO.[F:21][C:22]1[CH:23]=[C:24]([CH:36]=[CH:37][C:38]=1[F:39])[O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35].FC1C=C(C=CC=1F)OCCCCCCCCC(O)=O.Cl.Cl.[CH2:62]([O:69][C:70](=[O:78])[CH2:71][C@@H:72]([NH2:77])[CH2:73][N:74]([CH3:76])[CH3:75])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>>[CH2:62]([O:69][C:70](=[O:78])[CH2:71][C@@H:72]([NH:77][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:39])=[C:22]([F:21])[CH:23]=1)[CH2:73][N:74]([CH3:75])[CH3:76])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Participants

6

Reactant 5

HCID 759273,4-DifluorophenolHCID 1087001-Nonanol, 9-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66875233HCID 66875233, compoundHCID 66875376HCID 66875376, compound

Product 1

HCID 66875043HCID 66875043, compound

Procedure

The title compound, m/e=413.6 ([M−H]−), was produced in analogy with example 18, steps 1 to 4. Thus, 3,4-difluorophenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(3,4-difluoro-phenoxy)-nonan-1-ol, which was oxidized in step 2 to 9-(3,4-difluoro-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-(3,4-difluoro-phenoxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-b35a83134a9746ef83b36d428aa6b133
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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