氢氧化锂 → Porphyrin precursor

HRID 3096

反应方程式

HRID 3096 反应方程式
C([O:4][CH2:5][CH2:6][CH2:7][C:8]1[C:12]([CH3:13])=[C:11]([CH:14]=[O:15])[NH:10][C:9]=1[CH2:16][C:17]1[NH:18][C:19]([CH2:26][C:27]2[NH:28][C:29]([CH:40]=[O:41])=[C:30]([CH3:39])[C:31]=2[CH2:32][CH2:33][CH2:34][O:35]C(=O)C)=[C:20]([CH2:24][CH3:25])[C:21]=1[CH2:22][CH3:23])(=O)C.[Li+].[OH-]>CO>[CH:40]([C:29]1[NH:28][C:27]([CH2:26][C:19]2[NH:18][C:17]([CH2:16][C:9]3[NH:10][C:11]([CH:14]=[O:15])=[C:12]([CH3:13])[C:8]=3[CH2:7][CH2:6][CH2:5][OH:4])=[C:21]([CH2:22][CH3:23])[C:20]=2[CH2:24][CH3:25])=[C:31]([CH2:32][CH2:33][CH2:34][OH:35])[C:30]=1[CH3:39])=[O:41]

参与物

4

反应物 2

HCID 3939氢氧化锂HCID 543211662,5-Bis[(3-acetoxypropyl-5-formyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole

产物 1

HCID 11237009Porphyrin precursor收率 94%

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

7H, FIG. 7. 2,5-Bis[(3-acetoxypropyl-5-formyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole 7G (5.98 g, 0.011 mol) and LiOH (1.76 g, 0.042 mol) were added to 400 mL of 95% methanol, which had been degassed with nitrogen prior to use, add the mixture heated to reflux under a nitrogen atmosphere. The reaction became homogeneous when heated. After heating for 1.25 hours, the reaction was allowed to cool to room temperature. The product precipitated as a tan color solid as the reaction cooled. The volume of the reaction mixture was reduced to 75 mL on a rotary evaporator and the resulting slurry placed in the freezer for several hours. The product was filtered, and then purified by forming a slurry with 400 mL of methanol and 50 mL of water and heating close to boiling. The slurry was first cooled to room temperature, reduced to 1/2 volume under reduced pressure, and placed in the freezer for several hours. The product was collected by filtration and vacuum dried to yield 4.96 g of a tan powder (94%): 1H NMR (CD3OD, 300 MHz): δ0.96 (6H, t, CH2CH3), 1.49 (4H, p, CH2CH2CH2OH), 2.25 (6H, s, pyrrole-CH3), 2.32-2.43 (8H, m, CH2CH3 and CH2CH2CH2OH), 3.46 (4H, t, CH2CH2CH2OH), 3.85 (4H, s, (pyrrole)2 --CH2),9.34 (2H, s, CHO); CI MS (M+) 480; HRMS (M)+, 481.2942 (calc for C28H39N3O4, 481.2941).

后处理

  1. customhad been degassed with nitrogen
  2. additionadd the mixture
  3. temperatureheated
  4. temperatureto reflux under a nitrogen atmosphere
  5. temperatureheated
  6. temperatureAfter heating for 1.25 hours
  7. customThe product precipitated as a tan color solid as the reaction
  8. temperaturecooled
  9. customThe volume of the reaction mixture was reduced to 75 mL on a rotary evaporator
  10. waitthe resulting slurry placed in the freezer for several hours
  11. filtrationThe product was filtered
  12. custompurified
  13. customby forming a slurry with 400 mL of methanol and 50 mL of water
  14. temperatureheating
  15. customclose
  16. temperatureThe slurry was first cooled to room temperature
  17. waitplaced in the freezer for several hours
  18. filtrationThe product was collected by filtration and vacuum
  19. customdried

来源与证据

ORD记录
ord-712078ea7b614a19ba70e3fd5bf416de
来源数据集
uspto-grants-1998_03
专利号
US05733903

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