Dimethylamine → (S)-2-amino-3-(4-chloro-phenyl)-N,N-dimethyl-propionamide trifluoroacetate salt

HRID 1879483Notes

Reaction equation

HRID 1879483 reaction equation
CC(OC([NH:8][C@H:9]([C:18]([OH:20])=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)=O)(C)C.[CH3:21][NH:22][CH3:23].N[C@@H](CCSSCC[C@H](N)C(O)=O)C(O)=O.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[F:66][C:67]([F:72])([F:71])[C:68]([OH:70])=[O:69]>CN(C)C=O.ClCCl.C(OCC)(=O)C>[F:66][C:67]([F:72])([F:71])[C:68]([OH:70])=[O:69].[NH2:8][C@@H:9]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:18]([N:22]([CH3:23])[CH3:21])=[O:20]

Participants

10

Reactant 6

HCID 674DimethylamineHCID 6422Trifluoroacetic acidHCID 81531DiisopropylethylamineHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 439579L-HomocystineHCID 2734499N-(tert-Butoxycarbonyl)-4-chloro-L-phenylalanine

Product 1

HCID 67153258(S)-2-amino-3-(4-chloro-phenyl)-N,N-dimethyl-propionamide trifluoroacetate salt

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of Boc-L-4-chlorophenylalanine (Bachem California Inc., Torrance, Calif., USA; 5.0 g, 16.7 mmol), dimethylamine (2 M in tetrahydrofuran; 12.5 mL, 25 mmol), 1-hydroxybenzotriazole (available from 3B Scientific Corporation, Libertyville, Ill. 60048, USA; 2.69 g, 19.9 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluororophosphate (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 7.5 g, 19.8 mmol) and diisopropylethylamine (8.8 mL, 50.5 mmol) in N,N-dimethylformamide was stirred at 0° C. for 30 min and then at room temperature for 10 min. Ethyl acetate was added and the mixture was washed with water and brine. The organic phase was dried over sodium sulfate, filtered and evaporated to give a white solid. The solid was dissolved in dichloromethane (30 mL). Trifluoroacetic acid (30 mL) was added and the solution was stirred for 2 h at room temperature. The solvents were evaporated to give (S)-2-amino-3-(4-chloro-phenyl)-N,N-dimethyl-propionamide trifluoroacetate salt as a white solid.

Workup

  1. waitat room temperature for 10 min
  2. washthe mixture was washed with water and brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a white solid
  7. stirringthe solution was stirred for 2 h at room temperature
  8. customThe solvents were evaporated

Sources & evidence

ORD record
ord-1da3362da4224731bbf3695d855d1856
Source dataset
uspto-grants-2012_11
Patent number
US08314250B2

Reaction notes

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