3-Fluorobenzyl bromide → (R)-3-[8-(3-fluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester

HRID 1188223Notes

Reaction equation

HRID 1188223 reaction equation
C(O)CCCCCCCO.FC1C=C(C=CC=1)CBr.[F:20][C:21]1[CH:22]=[C:23]([CH:35]=[CH:36][CH:37]=1)[CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34].FC1C=C(C=CC=1)COCCCCCCCC(O)=O.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:33](=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][O:25][CH2:24][C:23]1[CH:35]=[CH:36][CH:37]=[C:21]([F:20])[CH:22]=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 680073-Fluorobenzyl bromideHCID 694201,8-OctanediolHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 668747688-(3-Fluoro-benzyloxy)-octan-1-olHCID 668749528-(3-Fluoro-benzyloxy)-octanoic acid

Product 1

HCID 66875163(R)-3-[8-(3-fluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester

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 3-fluorobenzyl bromide, leading to 8-(3-fluoro-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(3-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-(3-fluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-c6b835792e22495dac3c16ba637f9ecd
Source dataset
uspto-grants-2014_03
Patent number
US08673946B2

Reaction notes

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