1,8-Octanediol → HCID 66874637, compound

HRID 1188217Notes

Reaction equation

HRID 1188217 reaction equation
C(O)CCCCCCCO.BrCC1C=CC(C2C=CC=CC=2)=CC=1.[C:25]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:30]=[CH:29][C:28]([CH2:31][O: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(COCCCCCCCC(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][O:32][CH2:31][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 694201,8-OctanediolHCID 2577161,1'-Biphenyl, 4-(bromomethyl)-HCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 668754788-(Biphenyl-4-ylmethoxy)-octanoic acidHCID 668755858-(Biphenyl-4-ylmethoxy)-octan-1-ol

Product 1

HCID 66874637HCID 66874637, compound

Procedure

The title compound, m/e=455.3 ([M+H]+), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 4-(bromomethyl)-biphenyl, leading to 8-(biphenyl-4-ylmethoxy)-octan-1-ol, which was oxidized in step 2 to 8-(biphenyl-4-ylmethoxy)-octanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-3-[8-(biphenyl-4-ylmethoxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-30cf25f8e5494d0eb7435e604a74724b
Source dataset
uspto-grants-2014_03
Patent number
US08673946B2

Reaction notes

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