Methyl chloroformate → (2S,3S)-3-methoxy-2-(methoxycarbonylamino)butanoic acid

HRID 1471050ノート

反応式

HRID 1471050 の反応式
[CH3:1][O:2][C@H:3]([CH3:9])[C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5].Cl[C:11]([O:13][CH3:14])=[O:12]>C(=O)(O)[O-].[Na+]>[CH3:1][O:2][C@@H:3]([CH3:9])[C@H:4]([NH:5][C:11]([O:13][CH3:14])=[O:12])[C:6]([OH:8])=[O:7]

参加物

4

反応物 2

HCID 6586Methyl chloroformateHCID 2724875O-Methylthreonine

生成物 1

HCID 86649128(2S,3S)-3-methoxy-2-(methoxycarbonylamino)butanoic acid収率 86%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of allo-O-methyl-L-threonine (519 mg, 3.90 mmol) in saturated sodium bicarbonate solution (47.6 mL) was treated dropwise with methyl chloroformate (453 μL, 553 mg, 5.85 mmol) followed by stirring at RT for 18 h. The mixture was extracted with ether and the aqueous phase was cooled to 0° C. and acidified to pH 2-3 by addition of concentrated hydrochloric acid solution. The mixture was extracted with ethyl acetate (3×). The combined organic layers were extracted with saturated sodium chloride solution and dried (Na2SO4). Concentration in vacuo afforded the title compound (640 mg, 86%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 5.48 (d, J=7.8 Hz, 1H), 4.52 (d, J=4.7 Hz, 1H), 3.71 (s, 3H), 3.39 (s, 3H), 1.25 (t, J=7.6 Hz, 3H).

後処理

  1. extractionThe mixture was extracted with ether
  2. temperaturethe aqueous phase was cooled to 0° C.
  3. additionacidified to pH 2-3 by addition of concentrated hydrochloric acid solution
  4. extractionThe mixture was extracted with ethyl acetate (3×)
  5. extractionThe combined organic layers were extracted with saturated sodium chloride solution
  6. dry with materialdried (Na2SO4)
  7. concentrationConcentration in vacuo

出典と根拠

ORDレコード
ord-5d2f9ff49bfe4c2e8b8ceb47afbe662a
出典データセット
uspto-grants-2015_04
特許番号
US09006387B2

反応ノート

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