Diethyl Ether → 4-Aminomethylbenzyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate hydrochloride

HRID 248700Notes

Reaction equation

HRID 248700 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][CH:34]=1)[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH:24]C(OC(C)(C)C)=O)=[CH:19][CH:18]=1)=[O:14])=[O:8])(=[O:3])[CH3:2].C(OCC)C.[ClH:47].C(O)(=O)C>>[ClH:47].[C:1]([S:4][CH2:5][CH:6]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:32]=[CH:33][CH:34]=1)[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][NH2:24])=[CH:19][CH:18]=1)=[O:14])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 156702434-(t-Butyloxycarbonylaminomethyl)benzyl 3-[(2-acetylthiomethyl 3-phenylpropionyl)amino]benzoateHCID 22641269Acetate-hydrochloric acid

Product 1

HCID 197639264-Aminomethylbenzyl 3-[(2-acetylthiomethyl-3-phenylpropionyl)amino]benzoate hydrochloride

Procedure

4-(t-Butyloxycarbonylaminomethyl)benzyl 3-[(2-acetylthiomethyl 3-phenylpropionyl)amino]benzoate (compound of Example 121) (0.73 g) is dissolved in 1M hydrochloric acid-acetic acid solution (20 ml), and the mixture is reacted at room temperature for 45 minutes. The reaction mixture is added slowly to diethyl ether (100 ml) with stirring under ice cooling. The precipitates are separated by filtration and washed with diethyl ether to give the title compound (0.61 g). m.p.: 111°-113° C. (amorphous) IR (KBr; cm-1): 1710, 1685, 1650

Workup

  1. customthe mixture is reacted at room temperature for 45 minutes
  2. customThe precipitates are separated by filtration
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-65282e9cbde046ac865a254c9c81095b
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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