Phenol → HCID 66874106, compound

HRID 1799629Notes

Reaction equation

HRID 1799629 reaction equation
C1(O)C=CC=CC=1.BrCCCCCCCCCCCO.[O:21]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O(CCCCCCCCCCC(O)=O)C1C=CC=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:38](=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][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 996PhenolHCID 7416311-Bromo-1-undecanolHCID 8159711-Phenoxyundecanoic acidHCID 1157250211-Phenoxy-1-undecanolHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride

Product 1

HCID 66874106HCID 66874106, compound

Procedure

The title compound, m/e=405.7 ([M−H]−), was produced in analogy with example 18, steps 1 to 4. Thus, phenol was alkylated in step 1 with 11-bromo-1-undecanol, leading to 11-phenoxy-undecan-1-ol, which was oxidized in step 2 to 11-phenoxy-undecanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-4-dimethylamino-3-[11-phenoxy-undecanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-55bd7863525f44ccbd9d3d51e826be69
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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