Methyl chloroformate → N-(Methoxycarbonyl)-N-methyl-L-valine

HRID 1625519

반응식

HRID 1625519 반응식
[CH3:1][CH:2]([CH3:9])[C@H:3]([NH:7][CH3:8])[C:4]([OH:6])=[O:5].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+].Cl[C:19]([O:21][CH3:22])=[O:20]>>[CH3:22][O:21][C:19]([N:7]([CH3:8])[C@@H:3]([CH:2]([CH3:9])[CH3:1])[C:4]([OH:6])=[O:5])=[O:20]

참가 물질

5

반응물 4

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 444080N-Methyl-L-valine

생성물 1

HCID 59166373N-(Methoxycarbonyl)-N-methyl-L-valine수율 71%

실험 절차

(2S)-3-Methyl-2-methylamino-butanoic acid (5 g, 38.12 mmol) is added to a stirring solution of sodium hydroxide (76.2 mL of 1 M, 76.24 mmol). After complete dissolution, sodium carbonate (2.1 g, 19.82 mmol) is added followed by methyl chloroformate (3.18 mL, 41.17 mmol) at 0° C. over 40 minutes. The reaction mixture is stirred at rt for 4 hours, and then washed with diethyl ether (2×75 ml). The aqueous layer is cooled to 0° C., acidified to pH 1-2 and extracted with CH2Cl2. The organic phase is dried over MgSO4, filtered and concentrated to dryness to give the title compound (2S)-2-[methoxycarbonyl(methyl)amino]-3-methyl-butanoic acid (5.12 g, 71%) as a clear oil.

후처리

  1. additionis added
  2. washwashed with diethyl ether (2×75 ml)
  3. temperatureThe aqueous layer is cooled to 0° C.
  4. extractionextracted with CH2Cl2
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-0e144cec5c7d415a837449b592c9b4e0
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779156B2

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