2,6-Lutidine → N-(t-Butyldimethylsilyloxycarbonyl)-L-methionine methyl ester

HRID 1904446Notes

Reaction equation

HRID 1904446 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@H:4]([CH2:13][CH2:14][S:15][CH3:16])[NH:5][C:6]([O:8]C(C)(C)C)=[O:7].N1C(C)=CC=CC=1C.[Si:26](OS(C(F)(F)F)(=O)=O)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].[Cl-].[NH4+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C@H:4]([CH2:13][CH2:14][S:15][CH3:16])[NH:5][C:6]([O:8][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])=[O:7]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 11097398(S)-Methyl 2-((tert-butoxycarbonyl)amino)-4-(methylthio)butanoate

Product 1

HCID 13934327N-(t-Butyldimethylsilyloxycarbonyl)-L-methionine methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride solution (1.0 ml) of N-t-butoxycarbonyl-L-methionine methyl ester (131.5 mg, 0.5 mmol) and 2,6-lutidine (0.116 ml, 1.0 mmol), t-butyldimethylsilyltrifluoromethane sulfonate (TBDMSOTf) (0.172 ml, 0.75 mmol) was added dropwise at room temperature in a nitrogen atmosphere. After the mixture was stirred for 15 minutes, a saturated aqueous solution of ammonium chloride (2 ml) was added to quench the reaction and extraction with ether was conducted. The organic layer was dried over anhydrous magnesium sulfate and filtered. By distilling off the solvent under vacuum, the titled compound was obtained in an amount of 146 mg.

Workup

  1. customto quench
  2. customthe reaction and extraction with ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationBy distilling off the solvent under vacuum

Sources & evidence

ORD record
ord-54293b7aebdf400ea2dde9437087daa5
Source dataset
uspto-grants-1989_06
Patent number
US04837349

Reaction notes

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