Ethanol → 1-Ethyl (3E)-2-amino-4-methyl-5-phosphono-3-pentenoate

HRID 1682313노트

반응식

HRID 1682313 반응식
C[Si](C)(C)Br.[CH2:6]([O:8][C:9](=[O:28])[CH:10]([NH:25]C=O)/[CH:11]=[C:12](\[CH3:24])/[CH2:13][P:14]([O:20]C(C)C)([O:16]C(C)C)=[O:15])[CH3:7].C(O)C>ClCCl>[CH2:6]([O:8][C:9](=[O:28])[CH:10]([NH2:25])/[CH:11]=[C:12](\[CH3:24])/[CH2:13][P:14]([OH:16])([OH:20])=[O:15])[CH3:7]

참가 물질

5

반응물 3

HCID 702EthanolHCID 76113BromotrimethylsilaneHCID 86745094HCID 86745094, 화합물

생성물 1

HCID 63723341-Ethyl (3E)-2-amino-4-methyl-5-phosphono-3-pentenoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

56.7 ml of trimethylbromosilane are added dropwise within a period of 15 minutes at 20° to a solution of 25.42 g of E-2-formylamino-4-methyl-5-diisopropylphosphono-3-pentenoic acid ethyl ester in 102 ml of dry dichloromethane. After stirring at room temperature for 20 hours, 102 ml of ethanol are added dropwise within a period of 15 minutes, and the whole is stirred for a further 20 hours. The clear reaction solution is then completely concentrated by evaporation in vacuo. The residue is concentrated by evaporation a further three times in each case after the addition of 100 ml of toluene. The oily residue is dissolved in 102 ml of ethanol, and a solution of 102 ml of propylene oxide in 102 ml of ethanol is added dropwise thereto. The product, obtained in crystalline form, is filtered off after 2 hours (room temperature) and washed with ethanol and ether. After drying (80°, 4 hours) under a high vacuum, E-2-amino-4-methyl-5 -phosphono-3-pentenoic acid ethyl ester is obtained in analytically pure form, m.p. 212° (decomp.).

후처리

  1. stirringthe whole is stirred for a further 20 hours
  2. concentrationThe clear reaction solution is then completely concentrated by evaporation in vacuo
  3. concentrationThe residue is concentrated by evaporation a further three times in each case
  4. additionafter the addition of 100 ml of toluene
  5. dissolutionThe oily residue is dissolved in 102 ml of ethanol
  6. additiona solution of 102 ml of propylene oxide in 102 ml of ethanol is added dropwise
  7. customThe product, obtained in crystalline form
  8. filtrationis filtered off after 2 hours (room temperature)
  9. washwashed with ethanol and ether
  10. customAfter drying (80°, 4 hours) under a high vacuum

출처 및 근거

ORD 기록
ord-11d32d8fbdf8473d96f019a66c4f9ec6
출처 데이터셋
uspto-grants-1992_12
특허 번호
US05175344

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