Hydrochloric Acid → (S)-2-Amino-N-(3,4-dimethyl-phenyl)-N-[2-(5-methyl-pyridin-2-yl)-ethyl]-2-phenyl-acetamide dihydrochloride

HRID 1094360Notes

Reaction equation

HRID 1094360 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:15](=[O:34])[N:16]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([CH3:33])[CH:27]=1)[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(C)C.[ClH:36]>O1CCOCC1>[ClH:36].[ClH:36].[NH2:7][C@@H:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:15]([N:16]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([CH3:33])[CH:27]=1)[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][N:20]=1)=[O:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58007500((S)-{(3,4-dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-carbamoyl}-phenyl-methyl)-carbamic acid tert-butyl ester

Product 1

HCID 66638324(S)-2-Amino-N-(3,4-dimethyl-phenyl)-N-[2-(5-methyl-pyridin-2-yl)-ethyl]-2-phenyl-acetamide dihydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 50 mg (0.11 mmol) ((S)-{(3,4-dimethyl-phenyl)-[2-(5-methyl-pyridin-2-yl)-ethyl]-carbamoyl}-phenyl-methyl)-carbamic acid tert-butyl ester in 0.2 mL dioxane was added 265 uL (1.06 mmol) of a 4 M HCl solution in dioxane. The mixture was stirred at room temperature for 18 hours. The solvent was removed in vacuo. Ethylacetate was added and the mixture was stirred slowly at ambient temperature. The solid was filtered, rinsed with ether and dried under vacum to provide 0.044 g (94%) of the title compound as a light yellow solid MS (m/e): 374.3 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. additionEthylacetate was added
  3. stirringthe mixture was stirred slowly at ambient temperature
  4. filtrationThe solid was filtered
  5. washrinsed with ether
  6. customdried under vacum

Sources & evidence

ORD record
ord-5cca32afd15f4b7782340662653add78
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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