1-Butanol → L-Tyrosine, butanoate (ester)

HRID 2066339ノート

反応式

HRID 2066339 の反応式
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.S(=O)(=O)(O)O.[CH2:19]([OH:23])[CH2:20][CH2:21][CH3:22]>O.C1(C)C=CC=CC=1>[C:19]([O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C@@H:2]([C:11]([OH:13])=[O:12])[NH2:1])=[CH:9][CH:8]=1)(=[O:23])[CH2:20][CH2:21][CH3:22]

参加物

6

反応物 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 6057L-Tyrosine

生成物 1

HCID 66739174L-Tyrosine, butanoate (ester)

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1140Toluene溶媒

実験手順

18.19 g of tyrosine was suspended in a solution of 9.8 g of concentrated sulfuric acid, 40 mL water, 40 mL of butanol, and 200 mL of toluene in a 500 mL round bottom flask equipped with a condenser and a Dean-Stark apparatus. The resulting solution was heated at reflux temperature until no more water could be distilled. The resulting solution was cooled in an ice bath, which caused the solution to separate into two phases. The upper phase was discarded and the lower phase, an oily syrup, was retained. The syrup was mixed with sufficient 5% aqueous sodium bicarbonate solution to neutralize acidic impurities to provide a solid that was collected by filtration and washed with cold water. The resulting solid was re-crystallized in ethyl acetate.

後処理

  1. customequipped with a condenser
  2. temperatureThe resulting solution was heated
  3. distillationcould be distilled
  4. temperatureThe resulting solution was cooled in an ice bath
  5. customto separate into two phases
  6. additionThe syrup was mixed with sufficient 5% aqueous sodium bicarbonate solution
  7. customto provide a solid
  8. filtrationthat was collected by filtration
  9. washwashed with cold water
  10. customThe resulting solid was re-crystallized in ethyl acetate

出典と根拠

ORDレコード
ord-1a31d332e30247e68d564b21fa596304
出典データセット
uspto-grants-2012_10
特許番号
US08293253B2

反応ノート

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