Water → HCID 86606497、化合物

HRID 1994126ノート

反応式

HRID 1994126 の反応式
[OH:1][CH2:2][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[H-].[Na+].[CH3:23]I.O>C1COCC1>[CH3:23][O:1][CH2:2][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:10])([CH3:11])[CH3:9]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86606496tert-butyl N-[(2S)-1-{[(tert-butoxy)carbonyl]amino}-3-hydroxypropan-2-yl]carbamate

生成物 1

HCID 86606497HCID 86606497、化合物収率 36.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of di-tert-butyl [(2S)-3-hydroxypropane-1,2-diyl]biscarbamate (2.45 g, 8.10 mmol) in THF (80 mL) at 0° C., was added NaH (60%, 357 mg, 8.91 mmol). The reaction was allowed to stir at 0° C. for 30 min, and then methyl iodide (0.556 mL, 8.91 mmol) was added dropwise. The reaction was stirred at 0° C. for 1 h and then allowed to warm to rt and stirred for 3 h. Water was added and the reaction was extracted into EtOAc. The combined organic solutions were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography (SiO2, EtOAc/hexane) to yield the title compound as a white solid (895 mg, 36%).

後処理

  1. stirringThe reaction was stirred at 0° C. for 1 h
  2. temperatureto warm to rt
  3. stirringstirred for 3 h
  4. extractionthe reaction was extracted into EtOAc
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, EtOAc/hexane)

出典と根拠

ORDレコード
ord-ee55feace5ac4ee39d56176525e8efc7
出典データセット
uspto-grants-2010_01
特許番号
US07652041B2

反応ノート

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