Water → (2R)-N-methyl-2-((5R)-5-((2-naphthyl)methyl)-2-oxopiperazin-1-yl)-3-phenylpropionamide

HRID 366104Notes

Reaction equation

HRID 366104 reaction equation
[NH2:1][C@H:2]([CH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=1)[CH2:3][N:4]([C@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:10]([NH:12][CH3:13])=[O:11])[C:5](=[O:8])[CH2:6]Cl.C(=O)([O-])O.[Na+].O>CO>[CH3:13][NH:12][C:10](=[O:11])[C@H:9]([N:4]1[CH2:3][C@@H:2]([CH2:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)[NH:1][CH2:6][C:5]1=[O:8])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 54523801(2R)-2-(N-((2R)-2-Amino-3-(2-naphthyl)propyl)-N-chloroacetyl-amino)-N-methyl-3-phenylpropionamide

Product 1

HCID 54574578(2R)-N-methyl-2-((5R)-5-((2-naphthyl)methyl)-2-oxopiperazin-1-yl)-3-phenylpropionamideYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(2R)-2-(N-((2R)-2-Amino-3-(2-naphthyl)propyl)-N-chloroacetyl-amino)-N-methyl-3-phenylpropionamide (0.69 g, 1.58 mmol) was dissolved in methanol (14 ml) and sodium hydrogen carbonate (0.40 g, 4.73 mmol) and water (7 ml) were added. The mixture was stirred overnight at room temperature. The solvent was removed in vacuo and the residue was dissolved in a mixture of ethyl acetate (30 ml) and saturated aqueous sodium hydrogen carbonate (20 ml). The mixture was extracted with ethyl acetate (4×20 ml). The combined organic phases were dried (magnesium sulfate) and the solvent was removed in vacuo. The residue was chromatographed on silica (2×20 cm) using methylene chloride/methanol/25% aqueous ammonia (100:10:1) to afford 0.19 g of (2R)-N-methyl-2-((5R)-5-((2-naphthyl)methyl)-2-oxopiperazin-1-yl)-3-phenylpropionamide

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in a mixture of ethyl acetate (30 ml) and saturated aqueous sodium hydrogen carbonate (20 ml)
  3. extractionThe mixture was extracted with ethyl acetate (4×20 ml)
  4. dry with materialThe combined organic phases were dried (magnesium sulfate)
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed on silica (2×20 cm)

Sources & evidence

ORD record
ord-e5b30b812f0642638998fb8ab07536f7
Source dataset
uspto-grants-2000_10
Patent number
US06127354

Reaction notes

Loading…