1-Naphthol → HCID 66875482, compound

HRID 1799628Notes

Reaction equation

HRID 1799628 reaction equation
C1(O)C2C(=CC=CC=2)C=CC=1.BrCCCCCCCCCO.[C:23]1([O:33][CH2:34][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(OCCCCCCCCC(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][CH2:34][O: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 70051-NaphtholHCID 1087001-Nonanol, 9-bromo-HCID 21650055HCID 21650055, compoundHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 66874675HCID 66874675, compound

Product 1

HCID 66875482HCID 66875482, compound

Procedure

The title compound, m/e=429.5 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, naphthalen-1-ol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-(naphthalen-1-yloxy)-nonan-1-ol, which was oxidized in step 2 to 9-(naphthalen-1-yloxy)-nonanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-4-dimethylamino-3-[9-(naphthalen-1-yloxy)-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-c261562e5c844a5b83a3960722d468a1
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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