12-Phenyllauric acid → (R)-4-dimethylamino-3-(12-phenyl-dodecanoylamino)-butyric acid benzyl ester

HRID 1802991Notes

Reaction equation

HRID 1802991 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl.[CH2:23]([O:30][C:31](=[O:39])[CH2:32][C@@H:33]([NH2:38])[CH2:34][N:35]([CH3:37])[CH3:36])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([O:30][C:31](=[O:39])[CH2:32][C@@H:33]([NH:38][C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:34][N:35]([CH3:36])[CH3:37])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 15192212-Phenyllauric acidHCID 46223507(R)-benzyl 3-amino-4-(dimethylamino)butanoate dihydrochloride

Product 1

HCID 66875086(R)-4-dimethylamino-3-(12-phenyl-dodecanoylamino)-butyric acid benzyl ester

Procedure

The title compound, m/e=403.6 ([M−H]−), was produced in analogy with intermediate 1, steps 3 and 4. Thus, commercially available 12-phenyldodecanoic acid was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride to produce (R)-4-dimethylamino-3-(12-phenyl-dodecanoylamino)-butyric acid benzyl ester, which was hydrogenated in step 4.

Sources & evidence

ORD record
ord-27834df8312044188bf891ca108f5a31
Source dataset
uspto-grants-2013_01
Patent number
US08349893B2

Reaction notes

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