Water → 4-Tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester

HRID 491869ノート

反応式

HRID 491869 の反応式
[CH3:1][O:2][C:3]([CH2:5]P(OC)(OC)=O)=[O:4].[H-].[Na+].[C:14]([O:18][C:19](=[O:30])[NH:20][CH:21]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)[CH:22]=O)([CH3:17])([CH3:16])[CH3:15].O>C1COCC1>[CH3:1][O:2][C:3](=[O:4])[CH:5]=[CH:22][CH:21]([NH:20][C:19]([O:18][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:30])[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 23644230tert-butyl N-(1-cyclohexyl-2-oxoethyl)carbamate

生成物 1

HCID 670235054-Tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To an ice cooled solution of trimethyl phosphonoacetate (19 mL, 0.11 mol) in THF (200 mL) was added 60% NaH (3.1 g, 0.08 mol) in portions. The ice bath was removed and the reaction mixture was stirred at room temperature for 30 min. The reaction mixture was then cooled to 0° C. before a solution of (1-cyclohexyl-2-oxo-ethyl)-carbamic acid tert-butyl ester (9 g, 37 mmol) in THF (200 mL) was added. The reaction mixture was stirred at room temperature for another 20 min. Water (100 mL) was added, and then most of the THF was evaporated. The product was extracted with EtOAc (400 mL), and the organic layer was washed with aqueous NaCl solution and then dried with MgSO4. Evaporation yielded a residue which was purified by column chromatography (1:1 heptane:EtOAc) to yield 4-tert-butoxycarbonylamino-4-cyclohexyl-but-2-enoic acid methyl ester as a white solid.

後処理

  1. customThe ice bath was removed
  2. additionwas added
  3. stirringThe reaction mixture was stirred at room temperature for another 20 min
  4. custommost of the THF was evaporated
  5. extractionThe product was extracted with EtOAc (400 mL)
  6. washthe organic layer was washed with aqueous NaCl solution
  7. dry with materialdried with MgSO4
  8. customEvaporation
  9. customyielded a residue which
  10. customwas purified by column chromatography (1:1 heptane:EtOAc)

出典と根拠

ORDレコード
ord-9cb01b08a3ec4aa69db13fe5993441bb
出典データセット
uspto-grants-2009_05
特許番号
US07531545B2

反応ノート

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