1,8-Octanediol → (R)-3-[8-(2,3,4-trifluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester

HRID 1802963

Reaktionsgleichung

Reaktionsgleichung von HRID 1802963
C(O)CCCCCCCO.FC1C(F)=C(F)C=CC=1CBr.[F:22][C:23]1[C:39]([F:40])=[C:38]([F:41])[CH:37]=[CH:36][C:24]=1[CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35].FC1C(F)=C(F)C=CC=1COCCCCCCCC(O)=O.Cl.Cl.[CH2:65]([O:72][C:73](=[O:81])[CH2:74][C@@H:75]([NH2:80])[CH2:76][N:77]([CH3:79])[CH3:78])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1>>[CH2:65]([O:72][C:73](=[O:81])[CH2:74][C@@H:75]([NH:80][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][O:26][CH2:25][C:24]1[CH:36]=[CH:37][C:38]([F:41])=[C:39]([F:40])[C:23]=1[F:22])[CH2:76][N:77]([CH3:78])[CH3:79])[C:66]1[CH:71]=[CH:70][CH:69]=[CH:68][CH:67]=1

Komponenten

6

Edukt 5

HCID 694201,8-OctanediolHCID 27770501-(Bromomethyl)-2,3,4-trifluorobenzeneHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 668748068-(2,3,4-Trifluoro-benzyloxy)-octan-1-olHCID 668751248-(2,3,4-Trifluoro-benzyloxy)-octanoic acid

Produkt 1

HCID 66875595(R)-3-[8-(2,3,4-trifluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester

Versuchsvorschrift

The title compound, m/e=432.5 ([M+H]+), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 2,3,4-trifluorobenzyl bromide, leading to 8-(2,3,4-trifluoro-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(2,3,4-trifluoro-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-(2,3,4-trifluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Quellen und Nachweise

ORD-Eintrag
ord-d92dc750130c404588dfa78233b4d449
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349893B2

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