1,8-Octanediol → (R)-3-[8-(4-trifluoromethyl-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester

HRID 1188214Notes

Reaction equation

HRID 1188214 reaction equation
C(O)CCCCCCCO.FC(F)(F)C1C=CC(CBr)=CC=1.[F:23][C:24]([F:43])([F:42])[C:25]1[CH:41]=[CH:40][C:28]([CH2:29][O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])=[CH:27][CH:26]=1.FC(F)(F)C1C=CC(COCCCCCCCC(O)=O)=CC=1.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:38](=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][O:30][CH2:29][C:28]1[CH:40]=[CH:41][C:25]([C:24]([F:42])([F:43])[F:23])=[CH:26][CH:27]=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 694201,8-OctanediolHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 668749768-(4-Trifluoromethyl-benzyloxy)-octanoic acidHCID 668751898-(4-Trifluoromethyl-benzyloxy)-octan-1-ol

Product 1

HCID 66875111(R)-3-[8-(4-trifluoromethyl-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester

Procedure

The title compound, m/e=445.6 ([M−H]−), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 4-trifluoromethyl-benzyl bromide, leading to 8-(4-trifluoromethyl-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(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-(4-trifluoromethyl-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-78d2093802ef4bc59804079357cdf9b9
Source dataset
uspto-grants-2014_03
Patent number
US08673946B2

Reaction notes

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