Water → Methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate

HRID 329536ノート

反応式

HRID 329536 の反応式
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:18]([OH:20])=[O:19])[CH2:16][CH2:15][C:14](=[O:17])[O:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:23]I.O>CN(C)C=O>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:18]([O:20][CH3:23])=[O:19])[CH2:16][CH2:15][C:14](=[O:17])[O:13]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodide2 回HCID 24758Sodium hydrideHCID 31063662-(((Benzyloxy)carbonyl)amino)-5-oxotetrahydrofuran-2-carboxylic acid

生成物 1

HCID 13995237Methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate収率 92.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In 100 ml of dimethylformamide was dissolved 27.93 g of 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylic acid prepared by the method described in Journal of Organic Chemistry, 6, 878 (1941). To the solution was added 4.0 g of sodium hydride (60% oil), to which was then added 28.4 g of methyl iodide, followed by allowing the reaction to proceed at room temperature for 4 hours. To the resultant was added 28.4 g of methyl iodide, and the mixture was stirred for further 3 hours. The reaction mixture was added to water, which was subjected to extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous saline solution, successively, then dried (MgSO4). The solvent was distilled off, and precipitating crystals were collected by filtration, followed by washing with ether to give 27.25 g of methyl 2-benzyloxycarbonylamino-5-oxo-2-tetrahydrofurancarboxylate as colorless crystals, m.p. 134°-134.5° C.

後処理

  1. customprepared by the method
  2. customthe reaction
  3. extractionwas subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  5. dry with materiala saturated aqueous saline solution, successively, then dried (MgSO4)
  6. distillationThe solvent was distilled off
  7. customprecipitating crystals
  8. filtrationwere collected by filtration
  9. washby washing with ether

出典と根拠

ORDレコード
ord-2e40db9fd848438ea550803662dca851
出典データセット
uspto-grants-1990_01
特許番号
US04891427

反応ノート

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