tert-Butyl isocyanate → N-(t-butylaminocarbonyl)-beta-phenyl isoserine methyl ester

HRID 1106986노트

반응식

HRID 1106986 반응식
[CH3:1][O:2][C:3](=[O:14])[C@H:4]([OH:13])[C@H:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH2:6].[C:15]([N:19]=[C:20]=[O:21])([CH3:18])([CH3:17])[CH3:16].[N-]=C=O>C1COCC1>[CH3:1][O:2][C:3](=[O:14])[CH:4]([OH:13])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[NH:6][C:20]([NH:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21]

참가 물질

5

반응물 3

HCID 62412tert-Butyl isocyanateHCID 105034IsocyanateHCID 10176516(2R,3S)-3-Phenylisoserine methyl ester

생성물 1

HCID 22389502N-(t-butylaminocarbonyl)-beta-phenyl isoserine methyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(2R,3S)-β-phenyl-isoserine methyl ester (4.35 g, 22 mM) is dissolved in dry THF (100 mL) and the flask cooled to 0°. To the mixture is added t-butyl isocyanate (2.8 mL, 25 mM). TLC after 15 minutes shows some starting material left so additional isocyanate (0.5 mL) is added. TLC after 1 hour shows no starting material so the solvent is concentrated under reduced pressure to give the title compound, NMR (CDCl3, TMS) 1.27, 3.43, 3.81, 4.34, 4.48, 5.27, 5.32, 7.29 and 7.34 δ; MS (FAB-High Res.) theory for C15H22N2O4 --H=295.1658, found=295.1663.

후처리

  1. temperaturethe flask cooled to 0°
  2. additionis added
  3. waitTLC after 1 hour shows
  4. concentrationno starting material so the solvent is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-70f6a443be814b49ae2ff65ee66640fa
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06057452

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