Methanol → (S)-Methyl 2-(((benzyloxy)carbonyl)amino)butanoate

HRID 929934ノート

反応式

HRID 929934 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH3:17])[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18]O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH3:17])[C:13]([O:15][CH3:18])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 887MethanolHCID 7349998(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid

生成物 1

HCID 10444846(S)-Methyl 2-(((benzyloxy)carbonyl)amino)butanoate収率 48%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of (S)-2-(((benzyloxy)carbonyl)amino)butanoic acid (10.0 g, 42.1 mmol) in methanol (100 mL) and toluene (300 mL) was added dropwise at room temperature under argon trimethylsilyldiazomethane (23.2 mL, 46.4 mmol). After stirring at room temperature for 1 hour, the reaction mixture was concentrated and the residue was extracted with a solution of EtOAc and brine. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by column chromatography (120 g SiO2) using EtOAc in hexane from 0% to 30% in order to give the title compound (5.2 g, 48%) as a colorless oil. LC-MS: [M+H] 252.1; Rt 0.93 min; (LCMS method 1).

後処理

  1. concentrationthe reaction mixture was concentrated
  2. extractionthe residue was extracted with a solution of EtOAc and brine
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (120 g SiO2)

出典と根拠

ORDレコード
ord-e7fbe75c337a42d5b27d29a09f6dcf0f
出典データセット
uspto-grants-2016_03
特許番号
US09296733B2

反応ノート

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