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

HRID 1188213Notes

Reaction equation

HRID 1188213 reaction equation
C(O)CCCCCCCO.FC1C(CBr)=C(F)C(F)=C(F)C=1F.[F:24][C:25]1[C:30]([CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][OH:41])=[C:29]([F:42])[C:28]([F:43])=[C:27]([F:44])[C:26]=1[F:45].FC1C(COCCCCCCCC(O)=O)=C(F)C(F)=C(F)C=1F.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:40](=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][O:32][CH2:31][C:30]1[C:25]([F:24])=[C:26]([F:45])[C:27]([F:44])=[C:28]([F:43])[C:29]=1[F:42])[CH2:82][N:83]([CH3:84])[CH3:85])[C:72]1[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=1

Participants

6

Reactant 5

HCID 694201,8-OctanediolHCID 74484Pentafluorobenzyl bromideHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 871868378-(Pentafluoro-benzyloxy)-octanoic acidHCID 871943438-(Pentafluoro-benzyloxy)-octan-1-ol

Product 1

HCID 87187238(R)-3-[8-(pentafluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester

Procedure

The title compound, m/e=467.5 ([M−H]−), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with pentafluorobenzyl bromide, leading to 8-(pentafluoro-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(pentafluoro-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-(pentafluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-fe3cce20e90441dd9d0c7669cac08092
Source dataset
uspto-grants-2014_03
Patent number
US08673946B2

Reaction notes

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