Ethyl Acetoacetate → (R)-3-Azido-2-methylpropanoic acid, methyl ester

HRID 1360176ノート

反応式

HRID 1360176 の反応式
[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH3:11])[CH2:5]OS(C)(=O)=O.[N-:13]=[N+:14]=[N-:15].[Na+].C(OC(=O)CC(C)=O)C>CN(C)C=O>[CH3:1][O:2][C:3](=[O:12])[C@H:4]([CH3:11])[CH2:5][N:13]=[N+:14]=[N-:15]

参加物

5

反応物 3

HCID 8868Ethyl AcetoacetateHCID 33557Sodium AzideHCID 86621909methyl (2R)-2-methyl-3-[(methylsulfonyl)oxy]propanoate

生成物 1

HCID 150729(R)-3-Azido-2-methylpropanoic acid, methyl ester収率 32%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(R)-3-methanesulfonyloxy-2-methyl-propionic acid methyl ester was dissolved in 100 mL of dimethylformamide, and then 8.2 g (126 mmol) of sodium azide was added thereto at 60° C., followed by stirring for 24 hours. After addition of 400 mL of ethylacetoacetate and washing with water, an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and then the residue was purified by column chromatography to give 2 g (13.9 mmol) of the title compound in a yield of 32%.

後処理

  1. customat 60° C.
  2. washwashing with water
  3. dry with materialan organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-8e5757f8552a4b57b3ab41457b33320a
出典データセット
uspto-grants-2011_02
特許番号
US07879848B2

反応ノート

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