Trifluoroacetic acid → HCID 12023194, compound

HRID 2287904Notes

Reaction equation

HRID 2287904 reaction equation
C(O[C:6](=O)[N:7](C)[C@@H:8]([C:16]([N:18]([CH3:22])[N:19]([CH3:21])[CH3:20])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:21][N:19]([CH3:20])[N:18]([CH3:22])[C:16](=[O:17])[C@H:8]([NH:7][CH3:6])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10854286HCID 10854286, compound

Product 1

HCID 12023194HCID 12023194, compoundYield 148%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-methyl-N-[(1R)-2-phenyl-1-(N,N',N'-trimethylhydrazinocarbonyl)ethyl]carbamic acid tert-butyl ester (0.3 g, 0.89 mmol) in methylene chloride (1 ml) was added trifluoroacetic acid (1 ml) and the mixture was stirred for 30 min. The mixture was concentrated in vacuo, stripped three times with methylene chloride and suspended in methylene chloride:(methanol/ammonia) (1:1) (2 ml) and trifluoroammonium acetate precipitated. Then diethyl ether (10 ml) was added and the mixture was filtered and the filtrate was concentrated in vacuo to give 0.31 g of (2R)-2-methylamino-3-phenylpropionic acid trimethylhydrazide as an oil.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. custom(methanol/ammonia) (1:1) (2 ml) and trifluoroammonium acetate precipitated
  3. additionThen diethyl ether (10 ml) was added
  4. filtrationthe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6aedf158acca4ad495bfc14925a32749
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

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