Sulfuric Acid → tert-butyl (2S)-2-amino-3-(4-hydroxy-3-iodophenyl)propanoate

HRID 429913

反応式

HRID 429913 の反応式
[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]

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 4397443-Iodo-L-TyrosineHCID 516892Sodium Bicarbonate

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

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, 95:5 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.

後処理

  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)

出典と根拠

ORDレコード
ord-5fb542aab96648f592defa820e5599a9
出典データセット
uspto-grants-2001_11
特許番号
US06319702B1

関連ノート

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