Water → (2R)-N-Methyl-2-methylamino-3-(1-naphthyl)-N-((1R)-2-phenyl-1-(((tetrahydrofuran-2-yl)methyl)carbamoyl)ethyl)-propionamide

HRID 1601977Notes

Reaction equation

HRID 1601977 reaction equation
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:20](=[O:40])[N:21]([CH3:39])[C@@H:22]([C:30](=[O:38])[NH:31][CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][O:34]1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:39][N:21]([C@@H:22]([C:30](=[O:38])[NH:31][CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][O:34]1)[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:20](=[O:40])[C@H:8]([NH:7][CH3:6])[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 10555137Methyl-((1R)-1-(methyl-((1R)-2-phenyl-1-(((tetrahydrofuran-2-yl)methyl)carbamoyl)ethyl)carbamoyl)-2-(1 naphthyl)ethyl)carbamic acid tert butylester

Product 1

HCID 10838229(2R)-N-Methyl-2-methylamino-3-(1-naphthyl)-N-((1R)-2-phenyl-1-(((tetrahydrofuran-2-yl)methyl)carbamoyl)ethyl)-propionamideYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl-((1R)-1-(methyl-((1R)-2-phenyl-1-(((tetrahydrofuran-2-yl)methyl)carbamoyl)ethyl)carbamoyl)-2-(1-naphtyl)ethyl)carbamic acid tert butylester (0.84 g; 1.46 mmol) was dissolved in methylene chloride (3 mL) and trifluoroacetic acid (2 mL) was added. The reaction mixture was stirred for 5 min at roomtemperature. Water (3 mL) and methylene chloride (5 mL) was added. Sodium hydrogen carbonate (solid) was added until pH 8. The reaction mixture was extracted with methylene chloride (3×10 mL). The combined organic layers were dried (magnesium sulfate) and evaporated in vacuo to afford 0.68 g of (2R)-N-methyl-2-methylamino-3-(1-naphtyl)-N-((1R)-2-phenyl-1-((tetrahydrofuran-2-yl-methyl)carbamoyl)ethyl)propionamide.

Workup

  1. extractionThe reaction mixture was extracted with methylene chloride (3×10 mL)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-c3a390d31f8e429b89ab7cf0883904b8
Source dataset
uspto-grants-1999_11
Patent number
US05977178

Reaction notes

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