Phenol → (R)-4-dimethylamino-3-[9-phenoxy-nonanoylamino]-butyric acid benzyl ester

HRID 1799630Notes

Reaction equation

HRID 1799630 reaction equation
C1(O)C=CC=CC=1.BrCCCCCCCCCO.[O:19]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][OH:35])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O(CCCCCCCCC(O)=O)C1C=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][CH2:28][CH2:27][CH2:26][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=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 996PhenolHCID 1087001-Nonanol, 9-bromo-HCID 158876389-Phenoxy-nonanoic acidHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochlorideHCID 539602249-Phenoxy-nonan-1-ol

Product 1

HCID 66875403(R)-4-dimethylamino-3-[9-phenoxy-nonanoylamino]-butyric acid benzyl ester

Procedure

The title compound, m/e=379.4 ([M+H]+), was produced in analogy with example 18, steps 1 to 4. Thus, phenol was alkylated in step 1 with 9-bromo-1-nonanol, leading to 9-phenoxy-nonan-1-ol, which was oxidized in step 2 to 9-phenoxy-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-phenoxy-nonanoylamino]-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-7def954050ba4940a574e9124c14734a
Source dataset
uspto-grants-2013_01
Patent number
US08344027B2

Reaction notes

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