4-Methoxyphenol → HCID 66874873, compound

HRID 1799627Notes

Reaction equation

HRID 1799627 reaction equation
COC1C=CC(O)=CC=1.BrCCCCCCCCCO.[CH3:21][O:22][C:23]1[CH:39]=[CH:38][C:26]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37])=[CH:25][CH:24]=1.COC1C=CC(OCCCCCCCCC(O)=O)=CC=1.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:36](=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][O:27][C:26]1[CH:38]=[CH:39][C:23]([O:22][CH3:21])=[CH:24][CH:25]=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 90154-MethoxyphenolHCID 1087001-Nonanol, 9-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874311HCID 66874311, compoundHCID 68992473HCID 68992473, compound

Product 1

HCID 66874873HCID 66874873, compound

Procedure

The title compound, m/e=409.5 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, 4-methoxy-phenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(4-methoxy-phenoxy)-nonan-1-ol, which was oxidized in step 2 to 9-(4-methoxy-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-methoxy-phenoxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-670e1bb8f769479fa8dfe51f86024cab
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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