1,6-Hexanediol → HCID 66874516, compound

HRID 1799650Notes

Reaction equation

HRID 1799650 reaction equation
C(O)CCCCCO.BrCCCC1C=CC=CC=1.[C:19]1([CH2:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(CCCOCCCCCC(O)=O)C=CC=CC=1.Cl.Cl.[CH2:56]([O:63][C:64](=[O:72])[CH2:65][C@@H:66]([NH2:71])[CH2:67][N:68]([CH3:70])[CH3:69])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1>>[CH2:56]([O:63][C:64](=[O:72])[CH2:65][C@@H:66]([NH:71][C:34](=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][CH2:27][CH2:26][CH2:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:67][N:68]([CH3:69])[CH3:70])[C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=1

Participants

6

Reactant 5

HCID 123741,6-HexanediolHCID 12503(3-Bromopropyl)benzeneHCID 15123205HCID 15123205, compoundHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 64298818HCID 64298818, compound

Product 1

HCID 66874516HCID 66874516, compound

Procedure

The title compound, m/e=379.4 ([M+H]+), was produced in analogy with example 1, steps 1 to 4. Thus, 1,6-hexanediol was alkylated in step 1 with 1-bromo-3-phenylpropane, leading to 6-(3-phenyl-propoxy)-hexan-1-ol, which was oxidized in step 2 to 6-(3-phenyl-propoxy)-hexanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-4-dimethylamino-3-[6-(3-phenyl-propoxy)-hexanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-0c0777bb506640bcb1f3c223d645d290
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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