Trifluoroacetic acid → (2R)-3-Benzyloxy-N-methyl-2-(methylamino)-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)propionamide

HRID 1268561Notes

Reaction equation

HRID 1268561 reaction equation
C(O[C:6](=O)[N:7]([C@@H:9]([C:19](=[O:34])[N:20]([CH3:33])[C@@H:21]([C:29](=[O:32])[NH:30][CH3:31])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:12]([O:11][CH2:10][C@@H:9]([NH:7][CH3:6])[C:19]([N:20]([CH3:33])[C@@H:21]([C:29](=[O:32])[NH:30][CH3:31])[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:34])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10791Sodium SesquicarbonateHCID 516892Sodium BicarbonateHCID 10576806N-((1R)-2-Benzyloxy-1-(N-methyl-N-((1R)-1-methylcarbamoyl-2-phenylethyl)-carbamoyl)ethyl)N-methylcarbamic acid tert-butyl ester

Product 1

HCID 11794376(2R)-3-Benzyloxy-N-methyl-2-(methylamino)-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)propionamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-((1R)-2-Benzyloxy-1-(N-methyl-N-((1R)-1-methylcarbamoyl-2-phenylethyl)carbamoyl)ethyl)N-methylcarbamic acid tert-butyl ester (0.23 g; 0.476 mmol) was dissolved in methylene chloride (3 mL) and trifluoroacetic acid (3 mL) was added. The reaction mixture was stirred for 10 min at room temperature. Methylene chloride (50 mL), an aqueous solution of sodium hydrogen carbonate/sodium carbonate (pH 9) and sodium hydrogen carbonate (solid) were added to the reaction mixture until pH 9. The organic phase was dried (magnesium sulfate) and evaporated in vacuo to afford 0.182 g of (2R)-3-Benzyloxy-N-methyl-2-(methylamino)-N-((1R)-1-(methylcarbamoyl)-2-phenylethyl)propionamide.

Workup

  1. dry with materialThe organic phase was dried (magnesium sulfate)
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-ee9f96fea3a8442198719bf36d1d4ad8
Source dataset
uspto-grants-2003_04
Patent number
US06555570B2

Reaction notes

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