4-Hydroxybiphenyl → HCID 66875647, compound

HRID 1799624Notes

Reaction equation

HRID 1799624 reaction equation
C1(C2C=CC=CC=2)C=CC(O)=CC=1.BrCCCCCCCCCO.[C:25]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41])=[CH:27][CH:26]=1.C1(C2C=CC=CC=2)C=CC(OCCCCCCCCC(O)=O)=CC=1.Cl.Cl.[CH2:74]([O:81][C:82](=[O:90])[CH2:83][C@@H:84]([NH2:89])[CH2:85][N:86]([CH3:88])[CH3:87])[C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1>>[CH2:74]([O:81][C:82](=[O:90])[CH2:83][C@@H:84]([NH:89][C:40](=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:30][CH:29]=1)[CH2:85][N:86]([CH3:87])[CH3:88])[C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1

Participants

6

Reactant 5

HCID 71034-HydroxybiphenylHCID 1087001-Nonanol, 9-bromo-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874694HCID 66874694, compoundHCID 66874790HCID 66874790, compound

Product 1

HCID 66875647HCID 66875647, compound

Procedure

The title compound, m/e=455.3 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, biphenyl-4-ol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(biphenyl-4-yloxy)-nonan-1-ol, which was oxidized in step 2 to 9-(biphenyl-4-yloxy)-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-(biphenyl-4-yloxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-0e0593a326bb4f01aed84c05abcc8d75
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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