Water → HCID 54047743, compound

HRID 581195Notes

Reaction equation

HRID 581195 reaction equation
C(O[C:6](=O)[N:7]([C@H:9]([CH2:26][C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)[C:10]([N:12]1[CH2:17][CH2:16][NH:15][C:14](=[O:18])[C@H:13]1[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:11])C)(C)(C)C.FC(F)(F)C(O)=O.O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:19]([C@H:13]1[N:12]([C:10](=[O:11])[C@H:9]([NH:7][CH3:6])[CH2:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=2)[CH2:17][CH2:16][NH:15][C:14]1=[O:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 53872402HCID 53872402, compound

Product 1

HCID 54047743HCID 54047743, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-((1R)-2-((2R)-2-Benzyl-3-oxopiperazin-1-yl)-1-((2-naphthyl)methyl)- 2-oxoethyl)-N-methylcarbamic acid tert-butyl ester (0.405 g; 0.808 mmol) was dissolved in methylene chloride (5 ml) and trifluoroacetic acid (5 ml) and stirred 10 min at room temperature. Water (10 ml) and sodium hydrogencarbonate were added to pH 8. The reaction mixture was extracted with methylene chloride (2×30 ml), dried over magnesium sulfate and evaporated in vacuo to afford 0.302 g of (3R)-3-benzyl-4-((2R)-2-methylamino-3-(2-naphthyl)propionyl)piperazin-2-one.

Workup

  1. extractionThe reaction mixture was extracted with methylene chloride (2×30 ml)
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-2dc2c6a9d90643a89341f7ec9216c95b
Source dataset
uspto-grants-1999_07
Patent number
US05919777

Reaction notes

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