3,4-Dimethoxyphenol → HCID 66874620, compound

HRID 1799625Notes

Reaction equation

HRID 1799625 reaction equation
COC1C=C(O)C=CC=1OC.BrCCCCCCCCCO.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:39]=[CH:40][C:41]=1[O:42][CH3:43])[O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38].COC1C=C(C=CC=1OC)OCCCCCCCCC(O)=O.Cl.Cl.[CH2:68]([O:75][C:76](=[O:84])[CH2:77][C@@H:78]([NH2:83])[CH2:79][N:80]([CH3:82])[CH3:81])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>>[CH2:68]([O:75][C:76](=[O:84])[CH2:77][C@@H:78]([NH:83][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][C:27]1[CH:39]=[CH:40][C:41]([O:42][CH3:43])=[C:25]([O:24][CH3:23])[CH:26]=1)[CH2:79][N:80]([CH3:81])[CH3:82])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

6

Reactant 5

HCID 162513,4-DimethoxyphenolHCID 1087001-Nonanol, 9-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 668750509-(3,4-Dimethoxy-phenoxy)-nonanoic acidHCID 668751309-(3,4-Dimethoxy-phenoxy)-nonan-1-ol

Product 1

HCID 66874620HCID 66874620, compound

Procedure

The title compound, m/e=439.4 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, 3,4-dimethoxyphenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(3,4-dimethoxy-phenoxy)-nonan-1-ol, which was oxidized in step 2 to 9-(3,4-dimethoxy-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-dimethoxy-phenoxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-47ac72a6affb47c0931bf698b34bece5
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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