alpha-Bromo-o-fluorotoluene → HCID 66875008, compound

HRID 1802973Notes

Reaction equation

HRID 1802973 reaction equation
C(O)CCCCCCCO.FC1C=CC=CC=1CBr.[F:20][C:21]1[CH:37]=[CH:36][CH:35]=[CH:34][C:22]=1[CH2:23][O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][OH:33].FC1C=CC=CC=1COCCCCCCCC(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:32](=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][O:24][CH2:23][C:22]1[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=1[F:20])[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 67968alpha-Bromo-o-fluorotolueneHCID 694201,8-OctanediolHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874216HCID 66874216, compoundHCID 66874799HCID 66874799, compound

Product 1

HCID 66875008HCID 66875008, 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 2-fluorobenzyl bromide, leading to 8-(2-fluoro-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(2-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-(2-fluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-8ab6fb2d63a34fcc9c0ed32798d563e4
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Reaction notes

Loading…