1,8-Octanediol → HCID 66875117, compound

HRID 1799607Notes

Reaction equation

HRID 1799607 reaction equation
C(O)CCCCCCCO.COC1C=CC(CBr)=CC=1.[CH3:21][O:22][C:23]1[CH:39]=[CH:38][C:26]([CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37])=[CH:25][CH:24]=1.COC1C=CC(COCCCCCCCC(O)=O)=CC=1.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:36](=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][CH2:27][C:26]1[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:39][CH:38]=1)[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 1650214-Methoxybenzyl bromideHCID 11021838HCID 11021838, compoundHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66875096HCID 66875096, compound

Product 1

HCID 66875117HCID 66875117, compound

Procedure

The title compound, m/e=407.6 ([M−H]−), was produced in analogy with example 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 4-methoxy-benzyl bromide, leading to 8-(4-methoxy-benzyloxy)-octan-1-ol, which was oxidized in step 2 to 8-(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-(4-methoxy-benzyloxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-822619c868944a8494f7578e115a139c
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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