四氧化硫 → tert-butyl (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoate

HRID 369806

反应方程式

HRID 369806 反应方程式
[I:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[OH:14])[CH2:5][C@@H:6]([C:8]([OH:10])=[O:9])[NH2:7].OS(O)(=O)=O.[CH3:20][C:21](=[CH2:23])[CH3:22].C([O-])(O)=O.[Na+]>O1CCOCC1.O>[I:1][C:2]1[CH:3]=[C:4]([CH:11]=[CH:12][C:13]=1[OH:14])[CH2:5][C@@H:6]([C:8]([O:10][C:21]([CH3:23])([CH3:22])[CH3:20])=[O:9])[NH2:7]

参与物

7

反应物 4

HCID 1118四氧化硫HCID 8255异丁烯HCID 4397443-碘-D/L-酪氨酸HCID 516892碳酸氢钠

产物 1

HCID 57291941tert-butyl (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoate收率 58%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 312751,4-二氧六环溶剂

实验过程

A mixture of 5.0 g of 3-iodo-L-tyrosine (Aldrich) and 2.5 mL of conc. H2SO4 in 85 mL of 1,4-dioxane was added to 30 mL of liquid isobutylene (condensed at -78° C.) in a 300 mL pressure bottle. The vessel was stoppered and the contents stirred at RT. After 3 days the bottle was cooled in an ice water bath, opened and the solution poured into a mixture of 10 g of NaHCO3 in 150 mL of water. The resulting mixture was subjected to rotary evaporation to remove isobutylene and dioxane. A white solid resulted which was collected by filtration and dried in vacuo. Analysis by tlc (SiO2, CH2Cl2 :MeOH) indicated major and minor components at Rf= 0.52 and 0.60 respectively. The crude product was purified by flash chromatography on silica gel (95:5 CH2Cl2 :MeOH) to afford 3.4 g (58%) of tert-butyl 3-iodo-L-tyrosinate as a white crystalline solid, m.p. 158-159° C.

后处理

  1. temperatureAfter 3 days the bottle was cooled in an ice water bath
  2. customThe resulting mixture was subjected to rotary evaporation
  3. customto remove isobutylene and dioxane
  4. customA white solid resulted which
  5. filtrationwas collected by filtration
  6. customdried in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (95:5 CH2Cl2 :MeOH)

来源与证据

ORD记录
ord-de78570fcc1e40daa453c2d989971b60
来源数据集
uspto-grants-2000_10
专利号
US06140100

关联笔记

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