2,3-Difluorophenol → HCID 66874171, compound

HRID 1799620Notes

Reaction equation

HRID 1799620 reaction equation
FC1C(F)=CC=CC=1O.BrCCCCCCCCCO.[F:21][C:22]1[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:23]=1[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34].FC1C(F)=CC=CC=1OCCCCCCCCC(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: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:38]([F:39])[C:22]=1[F:21])[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 808792,3-DifluorophenolHCID 1087001-Nonanol, 9-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874755HCID 66874755, compoundHCID 66874800HCID 66874800, compound

Product 1

HCID 66874171HCID 66874171, compound

Procedure

The title compound, m/e=415.5 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, 2,3-difluorophenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(2,3-difluoro-phenoxy)-nonan-1-ol, which was oxidized in step 2 to 9-(2,3-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-(2,3-difluoro-phenoxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-89cad46e9dae44e8b388fb060f1e4c9c
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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