1,8-Octanediol → (R)-3-[8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester
Reaction equation
C(O)CCCCCCCO.FC1C=C(C=CC=1C(F)(F)F)CBr.[F:24][C:25]1[CH:26]=[C:27]([CH:39]=[CH:40][C:41]=1[C:42]([F:45])([F:44])[F:43])[CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38].FC1C=C(C=CC=1C(F)(F)F)COCCCCCCCC(O)=O.Cl.Cl.[CH2:71]([O:78][C:79](=[O:87])[CH2:80][C@@H:81]([NH2:86])[CH2:82][N:83]([CH3:85])[CH3:84])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1>>[CH2:71]([O:78][C:79](=[O:87])[CH2:80][C@@H:81]([NH:86][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][CH2:28][C:27]1[CH:39]=[CH:40][C:41]([C:42]([F:43])([F:44])[F:45])=[C:25]([F:24])[CH:26]=1)[CH2:82][N:83]([CH3:84])[CH3:85])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1Participants
6
Reactant 5
Product 1
Procedure
The title compound, m/e=463.5 ([M−H]−), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 3-fluoro-4-trifluoromethyl-benzyl bromide, leading to 8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-3-[8-(3-fluoro-4-trifluoromethyl-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.
Sources & evidence
- ORD record
- ord-579b31deae984857aecb4df941e6d225
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673946B2
Reaction notes
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