Dimethylamine, hydrochloride → (S)-(1-Dimethylcarbamoyl-3-phenyl-propyl)-carbamic acid tert-butyl ester

HRID 651150

Reaction equation

HRID 651150 reaction equation
Cl.[CH3:2][NH:3][CH3:4].[C:5]([O:9][C:10]([NH:12][C@@H:13]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:14](O)=[O:15])=[O:11])([CH3:8])([CH3:7])[CH3:6]>ClCCl.CN(C=O)C>[C:5]([O:9][C:10](=[O:11])[NH:12][C@H:13]([C:14](=[O:15])[N:3]([CH3:4])[CH3:2])[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 2

HCID 10473Dimethylamine, hydrochlorideHCID 7018726(2S)-2-(((tert-butoxy)carbonyl)amino)-4-phenylbutanoic acid

Product 1

HCID 54369423(S)-(1-Dimethylcarbamoyl-3-phenyl-propyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

Dimethylamine hydrochloride (1.0 mmol) and (S)-N-t-butoxycarbonyl-2-amino-4-phenylbutyric acid (0.84 mmol) were coupled according to Procedure A (0-25° C. reaction temperature, 3:1 dichloromethane/DMF reaction solvent) giving the product which was used without further purification. Yield 238 mg, 93%; HPLC (60/40) 5.98 minutes (97%).

Workup

  1. customgiving the product which
  2. customwas used without further purification
  3. customHPLC (60/40) 5.98 minutes (97%)

Sources & evidence

ORD record
ord-d0fc4e6efbfc443a85206233028fb153
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Linked notes

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