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

HRID 381781ノート

反応式

HRID 381781 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-e68aa05bd5be4b0d94993bc830cff8c9
出典データセット
uspto-grants-2001_10
特許番号
US06307064B1

反応ノート

読み込み中…