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

HRID 491869노트

반응식

HRID 491869 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-9cb01b08a3ec4aa69db13fe5993441bb
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531545B2

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