1,8-Octanediol → HCID 66874619, compound

HRID 1802971Notes

Reaction equation

HRID 1802971 reaction equation
C(O)CCCCCCCO.BrCC1C2C(=CC=CC=2)C=CC=1.[C:23]1([CH2:33][O:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][OH:43])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1.C1(COCCCCCCCC(O)=O)C2C(=CC=CC=2)C=CC=1.Cl.Cl.[CH2:68]([O:75][C:76](=[O:84])[CH2:77][C@@H:78]([NH2:83])[CH2:79][N:80]([CH3:82])[CH3:81])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1>>[CH2:68]([O:75][C:76](=[O:84])[CH2:77][C@@H:78]([NH:83][C:42](=[O:43])[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][O:34][CH2:33][C:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][CH:24]=1)[CH2:79][N:80]([CH3:81])[CH3:82])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

6

Reactant 5

HCID 694201,8-OctanediolHCID 1378441-(Bromomethyl)naphthaleneHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874844HCID 66874844, compoundHCID 66875377HCID 66875377, compound

Product 1

HCID 66874619HCID 66874619, compound

Procedure

The title compound, m/e=427.1 ([M−H]−), was produced in analogy with intermediate 1, steps 1 to 4. Thus, 1,8-octanediol was alkylated in step 1 with 1-bromomethyl-naphthalene, leading to 8-(naphthalen-1-ylmethoxy)-octan-1-ol, which was oxidized in step 2 to 8-(naphthalen-1-ylmethoxy)-octanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-3-[8-(naphthalen-1-ylmethoxy)-octanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-44a0cf809ea14598882701a36b8836a6
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Reaction notes

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