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

HRID 2364875노트

반응식

HRID 2364875 반응식
[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]

참가 물질

4

반응물 2

HCID 6586Methyl chloroformateHCID 2724875O-Methylthreonine

생성물 1

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

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

실험 절차

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, 1 H), 4.52 (d, J=4.7 Hz, 1 H), 3.71 (s, 3 H), 3.39 (s, 3 H), 1.25 (t, J=7.6 Hz, 3 H).

후처리

  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

출처 및 근거

ORD 기록
ord-4b94fa2ba5a946109fded6888022176e
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691938B2

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