1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-2-yl-acrylic acid methyl ester

HRID 19353

반응식

HRID 19353 반응식
[CH3:1][O:2][C:3](=[O:20])[CH:4](P(O)(O)=O)[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].N12CCCN=C1CCCCC2.[CH:32]12[CH2:38][CH:35]([CH2:36][CH2:37]1)[CH2:34][CH:33]2[CH:39]=O>ClCCl>[CH3:1][O:2][C:3](=[O:20])[C:4]([NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])=[CH:39][CH:33]1[CH2:34][CH:35]2[CH2:38][CH:32]1[CH2:37][CH2:36]2

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86864Bicyclo[2.2.1]heptane-2-carbaldehydeHCID 66895383N-(benzyloxycarbonyl)-alpha-phosphonoglycine methyl ester

생성물 1

HCID 668955732-Benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-2-yl-acrylic acid methyl ester수율 36.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

In a round bottom flask was placed N-(benzyloxycarbonyl)-α-phosphonoglycine methyl ester (2.05 g, 6.18 mmol) in dichloromethane (5 mL) and cooled to 0° C. in an ice bath. To this mixture was then added slowly 1,8-diazabicyclo[5.4.0]undec-7-ene (801 μL, 5.36 mmol) and it was stirred at 0° C. for 20 min. The mixture was then treated with a solution of bicyclo[2.2.1]heptane-2-carbaldehyde (512 mg, 4.12 mmol) in dichloromethane (5 mL). After the addition was complete, the mixture was allowed to warm to 25° C. and stirred overnight. The mixture was concentrated in vacuo and then dissolved in ethyl acetate (50 mL) and washed with a saturated aqueous ammonium chloride solution (2×25 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. Purification by AnaLogix IntelliFlash chromatography (25 g column, 15% ethyl acetate/hexanes to 34% ethyl acetate/hexanes) afforded 2-benzyloxycarbonylamino-3-bicyclo[2.2.1]hept-2-yl-acrylic acid methyl ester (491 mg, 36%) as a clear colorless oil.

후처리

  1. customIn a round bottom flask was placed
  2. additionAfter the addition
  3. temperatureto warm to 25° C.
  4. stirringstirred overnight
  5. concentrationThe mixture was concentrated in vacuo
  6. dissolutiondissolved in ethyl acetate (50 mL)
  7. washwashed with a saturated aqueous ammonium chloride solution (2×25 mL)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification by AnaLogix IntelliFlash chromatography (25 g column, 15% ethyl acetate/hexanes to 34% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-f3903de789ea44f0b69e74904d176209
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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