Trifluoroacetic acid → HCID 53992856, compound

HRID 2287887Notes

Reaction equation

HRID 2287887 reaction equation
[C:1]([O:5][C:6](=O)[N:7]([C@H:9]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:10]([NH:12][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].[CH3:6][NH:7][C@H:9]([CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:10]([NH:12][NH:13][C:14](=[O:16])[CH3:15])=[O:11]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10759234HCID 10759234, compound

Product 2

HCID 21705897Ammonia methanolHCID 53992856HCID 53992856, compoundYield 144%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-[(1R)-2-(N'-Acetylhydrazino)-1-benzyl-2-oxoethyl]-N-methylcarbamic acid tert-butyl ester (0.81 g, 2.42 mmol) was dissolved in methylene chloride (5 ml) and trifluoroacetic acid (5 ml) was added and the mixture was stirred for 30 min at room temperature. The mixture was concentrated in vacuo and stripped three times with methylene chloride and the remaining oil was chromatographed on silica (40 g) with methylene chloride:(methanol/ammonia) (9:1) to give 0.41 g of acetic acid N'-((2R)-2-(methylamino)-3-phenylpropionyl)hydrazide as an amorphous powder.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe remaining oil was chromatographed on silica (40 g) with methylene chloride

Sources & evidence

ORD record
ord-e36e6d775033455dae3568658b20d1c9
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

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