2,6-Lutidine → N-t-butyldimethylsilyloxycarbonylvaline methyl ester

HRID 1904445ノート

反応式

HRID 1904445 の反応式
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH:13]([CH3:15])[CH3:14])[NH:5][C:6]([O:8]C(C)(C)C)=[O:7].N1C(C)=CC=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>[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH:13]([CH3:14])[CH3:15])[NH:5][C:6]([O:8][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])=[O:7]

参加物

6

反応物 4

HCID 79372,6-LutidineHCID 25517Ammonium ChlorideHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 11031717N-(tert-Butoxycarbonyl)-L-valine methyl ester

生成物 1

HCID 13934325N-t-butyldimethylsilyloxycarbonylvaline methyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a methylene chloride solution (1.0 ml) of N-t-butoxycarbonyl-L-valine methyl ester (115.5 mg, 0.5 mmol) and 2,6-lutidine (0.116 ml, 1.0 mmol) was added dropwise t-butyldimethylsilyltrifluoromethane sulfonate (0.172 ml, 0.75 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 153.2 mg.

後処理

  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

出典と根拠

ORDレコード
ord-b943ef89acb54ada8861d8394caf3533
出典データセット
uspto-grants-1989_06
特許番号
US04837349

反応ノート

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