Trifluoroacetic acid → HCID 54359131, compound

HRID 2287891Notes

Reaction equation

HRID 2287891 reaction equation
[C:1]([O:5][C:6](=O)[N:7]([C@H:9]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:10]([N:12]([CH3:17])[NH:13][C:14](=[O:16])[CH3:15])=[O:11])C)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][OH:5].[NH3:7].[CH3:17][N:12]([C:10](=[O:11])[C@H:9]([NH:7][CH3:6])[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:13][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10807725HCID 10807725, compound

Product 2

HCID 21705897Ammonia methanolHCID 54359131HCID 54359131, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1R)-2-(N'-acetyl-N-methylhydrazino)-1-benzyl-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester (0.35 g, 1.00 mmol) in methylene chloride (2 ml) was added trifluoroacetic acid (2 ml) and the mixture was stirred for 30 min. The mixture was concentrated in vacuo and stripped three times with methylene chloride and chromatographed on silca gel (40 g) with methylene chloride:(methanol/ammonia) (9:1) to give 110 mg (44%) of acetic acid N'-methyl-N'-((2R)-2-(methylamino)-3-phenylpropionyl)hydrazide as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customchromatographed on silca gel (40 g) with methylene chloride

Sources & evidence

ORD record
ord-7fa52a0956e84f089e70932372eb825b
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

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