Benzyl Bromide → (R)-3-(10-benzyloxy-decanoylamino)-4-dimethylamino-butyric acid benzyl ester

HRID 1799657Notes

Reaction equation

HRID 1799657 reaction equation
C(O)CCCCCCCCCO.C(Br)C1C=CC=CC=1.[CH2:21]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCCCCCCCCCC(O)=O)C1C=CC=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:38](=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][O:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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 7498Benzyl BromideHCID 371531,10-DecanediolHCID 110108641-Decanol, 10-(phenylmethoxy)-HCID 2058189810-Benzyloxydecanoic acidHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride

Product 1

HCID 66875602(R)-3-(10-benzyloxy-decanoylamino)-4-dimethylamino-butyric acid benzyl ester

Procedure

The title compound, m/e=405.6 ([M−H]−), was produced in analogy with example 1, steps 1 to 4. Thus, 1,10-decanediol was alkylated in step 1 with benzyl bromide, leading to 10-benzyloxy-decan-1-ol, which was oxidized in step 2 to 10-benzyloxydecanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-3-(10-benzyloxy-decanoylamino)-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-c08ff2c096d649259d65fc8aa9a10594
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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