1,8-Octanediol → HCID 66874750, compound

HRID 1188210Notes

Reaction equation

HRID 1188210 reaction equation
C(O)CCCCCCCO.FC1C=CC(F)=CC=1CBr.[F:21][C:22]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:23]=1[CH2:24][O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][OH:34].FC1C=CC(F)=CC=1COCCCCCCCC(O)=O.Cl.Cl.[CH2:62]([O:69][C:70](=[O:78])[CH2:71][C@@H:72]([NH2:77])[CH2:73][N:74]([CH3:76])[CH3:75])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1>>[CH2:62]([O:69][C:70](=[O:78])[CH2:71][C@@H:72]([NH:77][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]=[C:36]([F:39])[CH:37]=[CH:38][C:22]=1[F:21])[CH2:73][N:74]([CH3:75])[CH3:76])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1

Participants

6

Reactant 5

HCID 694201,8-OctanediolHCID 5228302-(Bromomethyl)-1,4-difluorobenzeneHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 668753838-(2,5-Difluoro-benzyloxy)-octanoic acidHCID 668755838-(2,5-Difluoro-benzyloxy)-octan-1-ol

Product 1

HCID 66874750HCID 66874750, compound

Procedure

The title compound, m/e=413.3 ([M−H]−), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 2,5-difluorobenzyl bromide, leading to 8-(2,5-difluoro-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(2,5-difluoro-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-(2,5-difluoro-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-13e22458441b42eaa2b839ca62374cbc
Source dataset
uspto-grants-2014_03
Patent number
US08673946B2

Reaction notes

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