Chloroform → Tesmilifene Hydrochloride

HRID 1440956Notes

Reaction equation

HRID 1440956 reaction equation
C(Cl)(Cl)[Cl:2].[N+](C([N+]([O-])=O)(C)C(N[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C(O)=O)([O-])=O.[CH3:24][N:25]1[CH2:30][CH2:29]O[CH2:27][CH2:26]1.Cl[C:32]([O:34][CH2:35][CH:36]([CH3:38])C)=O.C(N[C@H:47]([C:53](O)=O)[CH2:48][CH2:49]CCN)(OC(C)(C)C)=O>>[CH3:27][CH2:26][N:25]([CH2:24][CH2:32][O:34][C:35]1[CH:36]=[CH:38][C:48]([CH2:49][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:47][CH:53]=1)[CH2:30][CH3:29].[ClH:2]

Participants

6

Reactant 5

HCID 6212ChloroformHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 2733284epsilon-tert-Butyloxycarbonyl-lysineHCID 131719346Dinitrophenylaminobutyric acid

Product 1

HCID 175534Tesmilifene Hydrochloride

Procedure

To 5 ml of chloroform dissolving 50 mg (0.19 mmol) of dinitrophenylaminobutyric acid (mfd. by Sigma Chemical Co.), 40.8 μl (0.38 mmol) of N-methylmorpholine (mfd. by Wako Pure Chemical Industries, Ltd.) and 36.1 μl (0.29 mmol) of isobutyl chloroformate (mfd. by Wako Pure chemical Industries, Ltd.) were added and reacted at 0° C. for 30 minutes with stirring. To this, 120 mg (0.13 mmol) of the Nα --BOC--L-lysine.DPPE condensate obtained in above i) was was added and reacted at room temperature overnight with stirring. After the reaction, the solvent was removed by distillation, followed by purification using a silica gel column (eluent: a mixed solvent of chloroform and methanol) to give 82 mg of Nα --BOC--Nε -dinitrophenyl-L-lysine.DPPE condensate (yield 54%).

Workup

  1. customreacted at 0° C. for 30 minutes

Sources & evidence

ORD record
ord-2f1cdd40d43a4c8e8f335b82f08e3327
Source dataset
uspto-grants-1996_03
Patent number
US05501953

Reaction notes

Loading…