1,4-Dioxane → N-tert-Butoxycarbonyl-3-tert-butyl-D-alanine methyl ester

HRID 2237367ノート

反応式

HRID 2237367 の反応式
[C:1]([O:5][C:6]([NH:8]/[C:9](=[CH:14]\[C:15]([CH3:18])([CH3:17])[CH3:16])/[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O1CCOCC1.[H][H]>C(O)C>[CH3:13][O:12][C:10](=[O:11])[C@@H:9]([CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7]

参加物

5

反応物 3

HCID 312751,4-DioxaneHCID 59302433Methyl (Z)-2-[(tert-butoxycarbonyl)amino]-4,4-dimethylpent-2-enoateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 59302429N-tert-Butoxycarbonyl-3-tert-butyl-D-alanine methyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Methyl (2Z)-2-[(tert-butoxycarbonyl)amino]-4,4-dimethylpent-2-enoate (Example 4A, 60 g, 233.2 mmol) is dissolved in ethanol p.a./dioxane 3:1 (1000 ml). Argon is passed through for about 10 min using a cannula. The solution is placed into an ultrasound bath (about 5 min), and (+)-1,2-bis[(2R,5R)diethylphospholano]benzene(cyclooctadiene)rhodium(I) triflate (600 mg, 1% by weight) is added. The mixture is hydrogenated under 3.5 bar hydrogen pressure and at RT for 3 days. The reaction mixture is filtered through kieselguhr and the eluate is concentrated. The crude product is chromatographed (silica gel, eluent: cyclohexane/ethyl acetate 4:1). 60 g (99% of theory) of the title compound are obtained.

後処理

  1. customis passed through for about 10 min
  2. customThe solution is placed into an ultrasound bath
  3. filtrationThe reaction mixture is filtered through kieselguhr
  4. concentrationthe eluate is concentrated
  5. customThe crude product is chromatographed (silica gel, eluent: cyclohexane/ethyl acetate 4:1)

出典と根拠

ORDレコード
ord-ac60d7ad70144731aed4b46461b99a54
出典データセット
uspto-grants-2010_05
特許番号
US07718611B2

反応ノート

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