Ethyl formate → (2S)-2-formylamino-propionic acid tert-butyl ester

HRID 602927ノート

反応式

HRID 602927 の反応式
Cl.[C:2]([O:6][C:7](=[O:11])[C@H:8]([CH3:10])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(C(C)C)CC)(C)C.[CH:21](OCC)=[O:22]>C(Cl)Cl>[C:2]([O:6][C:7](=[O:11])[C@@H:8]([NH:9][CH:21]=[O:22])[CH3:10])([CH3:5])([CH3:4])[CH3:3]

参加物

5

反応物 3

HCID 8025Ethyl formateHCID 81531DiisopropylethylamineHCID 11275390tert-Butyl alaninate hydrochloride

生成物 1

HCID 79006784(2S)-2-formylamino-propionic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a suspension of (2S) alanine tert-butyl ester hydrochloride (3.63 g, 20 mmol) in a mixture of ethyl formate (10 mL) and DCM (5 mL) was added diisopropylethylamine (3.83 mL, 22 mmol) and the reaction mixture was refluxed overnight. The solvents were evaporated and the residue was then triturated in Et2O and filtrated. The filtrates were evaporated and the residue was filtered through a short pad of silica using ethyl acetate as eluent. Evaporation of the solvent afforded the sub-title compound as a colorless oil which crystallised upon standing (2.806 g, 81%): 1H NMR (400 MHz CDCl3) δ 1.43 (3H, d), 1.50 (9H, s), 4.55 (1H, m), 6.31 (1H, br s), 8.16 (1H, s).

後処理

  1. temperaturethe reaction mixture was refluxed overnight
  2. customThe solvents were evaporated
  3. customthe residue was then triturated in Et2O
  4. filtrationfiltrated
  5. customThe filtrates were evaporated
  6. filtrationthe residue was filtered through a short pad of silica
  7. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-1dd566a3561044b79407989becf4d1d7
出典データセット
uspto-grants-2011_03
特許番号
US07906650B2

反応ノート

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