2,6-Lutidine → HCID 70389300, compound

HRID 1904443Notes

Reaction equation

HRID 1904443 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C@:4]([NH2:28])([C@@H:13]([CH2:21][C:22](=[O:27])[CH:23]=[CH:24][CH2:25][CH3:26])[O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[NH:5][C:6]([O:8]C(C)(C)C)=[O:7].N1C(C)=CC=CC=1C.[Si:38](OS(C(F)(F)F)(=O)=O)([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39].[Cl-].[NH4+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:29])[C@:4]([NH2:28])([C@@H:13]([CH2:21][C:22](=[O:27])[CH:23]=[CH:24][CH2:25][CH3:26])[O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[NH:5][C:6]([O:8][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])=[O:7]

Participants

6

Reactant 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 70389903HCID 70389903, compound

Product 1

HCID 70389300HCID 70389300, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methylene chloride solution (1.0 ml) of N-(t-butoxycarbonyl)-2-amino-4-pentenoyl-O-(tetrahydropyranyl)threonine methyl ester (37 mg, 0.09 mmol) and 2,6-lutidine (0.021 ml, 0.18 mmol) was added dropwise t-butyldimethylsilyltrifluoromethane sulfonate (TBDMSOTf) (0.031 ml, 0.14 mmol) 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 45.8 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 under vacuum

Sources & evidence

ORD record
ord-d8a3bfdb829e4583b9d288c96d87d181
Source dataset
uspto-grants-1989_06
Patent number
US04837349

Reaction notes

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