Ammonia → Butanedioic acid, 1,4-di-2-propen-1-yl ester

HRID 1635114

반응식

HRID 1635114 반응식
[C:1]([O-:8])(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=[O:5].CN(C(ON1N=NC2[CH:20]=[CH:21][CH:22]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:33](N(C(C)C)CC)([CH3:35])[CH3:34].N>CN(C=O)C>[CH2:35]([O:5][C:4](=[O:6])[CH2:3][CH2:2][C:1]([O:8][CH2:22][CH:21]=[CH2:20])=[O:7])[CH:33]=[CH2:34]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 81531DiisopropylethylamineHCID 160419SuccinateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 70215Butanedioic acid, 1,4-di-2-propen-1-yl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

11 (240 mg, 0.46 mmol) and HATU (350 mg, 0.92 mmol) were dissolved in DMF (2 mL) and diisopropylethylamine (0.16 mL, 0.92 mmol) was added. The mixture was stirred for 15 min at ambient temperature, and then treated with anhydrous ammonia for 20 min. Stirring was continued overnight. DMF was removed in vacuo, and the residue was diluted with ethyl acetate, washed with water and brine, then dried over MgSO4. After evaporation of the solvent, the residue was purified on silica gel (5% methanol/methylene chloride) to afford product 12 as a white solid. 12, a mixture of two diastereomers, was then separated on silica gel, using increasing gradient of 20-50% ethyl acetate-methylene chloride, to give first eluting isomer 12a (43 mg, 18%) and the second eluting isomer 12b (61 mg, 25%) both as a white solids. 12a: MS m/z 521.2 (MH+). 12b: MS m/z 521.2 (MH+).

후처리

  1. stirringStirring
  2. waitwas continued overnight
  3. customDMF was removed in vacuo
  4. additionthe residue was diluted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customAfter evaporation of the solvent
  8. customthe residue was purified on silica gel (5% methanol/methylene chloride)

출처 및 근거

ORD 기록
ord-2e9162714d7b4ab5a5d53fa9d1dec73b
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06509333B2

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