1,8-Octanediol → HCID 86635478, compound

HRID 1799610Notes

Reaction equation

HRID 1799610 reaction equation
C(O)CCCCCCCO.FC1C(F)=C(OC)C(F)=C(F)C=1CBr.[F:25][C:26]1[C:42]([F:43])=[C:41]([O:44][CH3:45])[C:40]([F:46])=[C:39]([F:47])[C:27]=1[CH2:28][O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38].FC1C(F)=C(OC)C(F)=C(F)C=1COCCCCCCCC(O)=O.Cl.Cl.[CH2:74]([O:81][C:82](=[O:90])[CH2:83][C@@H:84]([NH2:89])[CH2:85][N:86]([CH3:88])[CH3:87])[C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1>>[CH2:74]([O:81][C:82](=[O:90])[CH2:83][C@@H:84]([NH:89][C:37](=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][O:29][CH2:28][C:27]1[C:26]([F:25])=[C:42]([F:43])[C:41]([O:44][CH3:45])=[C:40]([F:46])[C:39]=1[F:47])[CH2:85][N:86]([CH3:87])[CH3:88])[C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1

Participants

6

Reactant 5

HCID 694201,8-OctanediolHCID 27752761-(Bromomethyl)-2,3,5,6-tetrafluoro-4-methoxybenzeneHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 86635479HCID 86635479, compoundHCID 86635480HCID 86635480, compound

Product 1

HCID 86635478HCID 86635478, compound

Procedure

The title compound, m/e=479.4 ([M−H]−), was produced in analogy with example 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 2,3,5,6-tetrafluoro-4-methoxy-benzyl bromide, leading to 8-(2,3,5,6-tetrafluoro-4-methoxy-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(2,3,5,6-tetrafluoro-4-methoxy-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-(2,3,5,6-tetrafluoro-4-methoxy-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-138fe07ed17d47799bd8c99d316e1a5b
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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