4-Fluorobenzyl bromide → HCID 66875253, compound

HRID 1188224Notes

Reaction equation

HRID 1188224 reaction equation
C(O)CCCCCCCO.FC1C=CC(CBr)=CC=1.[F:20][C:21]1[CH:37]=[CH:36][C:24]([CH2:25][O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])=[CH:23][CH:22]=1.FC1C=CC(COCCCCCCCC(O)=O)=CC=1.Cl.Cl.[CH2:59]([O:66][C:67](=[O:75])[CH2:68][C@@H:69]([NH2:74])[CH2:70][N:71]([CH3:73])[CH3:72])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1>>[CH2:59]([O:66][C:67](=[O:75])[CH2:68][C@@H:69]([NH:74][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:23]=[CH:22][C:21]([F:20])=[CH:37][CH:36]=1)[CH2:70][N:71]([CH3:72])[CH3:73])[C:60]1[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=1

Participants

6

Reactant 5

HCID 680214-Fluorobenzyl bromideHCID 694201,8-OctanediolHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874733HCID 66874733, compoundHCID 66875027HCID 66875027, compound

Product 1

HCID 66875253HCID 66875253, compound

Procedure

The title compound, m/e=397.4 ([M+H]+), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 4-fluorobenzyl bromide, leading to 8-(4-fluoro-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(4-fluoro-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-fluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-5a1e1289dff746c9aafc361c4838ceb8
Source dataset
uspto-grants-2014_03
Patent number
US08673946B2

Reaction notes

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