2,6-Lutidine → HCID 14765842, compound

HRID 1904444Notes

Reaction equation

HRID 1904444 reaction equation
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5](CC=C)[C:6]([O:8]C(C)(C)C)=[O:7].N1[C:22]([CH3:23])=[CH:21]C=CC=1C.[Si:25](OS(C(F)(F)F)(=O)=O)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26].[Cl-].[NH4+]>C(Cl)Cl>[Si:25]([O:8][C:6]([NH:5][CH:4]([CH2:23][CH:22]=[CH2:21])[C:3]([O:2][CH3:1])=[O:16])=[O:7])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 22243128N-Boc-allylglycine methyl ester

Product 1

HCID 14765842HCID 14765842, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride solution (1.5 ml) of N-(t-butoxycarbonyl)-allylglycine methyl ester (183 mg, 0.8 mmol) and 2,6-lutidine (0.186 ml, 1.6 mmol) was added t-butyldimethylsilyltrifluoromethane sulfonate (TBDMSOTf) (0.275 ml, 1.2 mmol) at room temperature in a nitrogen atmosphere. After the mixture was stirred for 15 minutes, a saturated aqueous solution of ammonium chloride (3 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 260 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-9ddae1b29bce4278a1064e3de9d1ce72
Source dataset
uspto-grants-1989_06
Patent number
US04837349

Reaction notes

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