2,6-Lutidine → HCID 13934329, compound

HRID 1904447Notes

Reaction equation

HRID 1904447 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:5][C:6]([O:8]C(C)(C)C)=[O:7].N1C(C)=CC=CC=1C.[Si:29](OS(C(F)(F)F)(=O)=O)([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30].[Cl-].[NH4+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[NH:5][C:6]([O:8][Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])=[O:7]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 9882138Boc-L-phenylalanine methyl ester

Product 1

HCID 13934329HCID 13934329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride solution (1.0 ml) of N-t-butoxycarbonyl-L-phenylalanine methyl ester (139.5 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, the titled compound was obtained in an amount of 186.8 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

Sources & evidence

ORD record
ord-a3ef608ff086417c8fb1ba45af8c7a68
Source dataset
uspto-grants-1989_06
Patent number
US04837349

Reaction notes

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