Trifluoroacetic acid → L-Valyl-N-Methyl-L-Alanyl-L-Alanine Benzyl Ester

HRID 2072757ノート

反応式

HRID 2072757 の反応式
[CH2:1]([O:8][C:9](=[O:33])[C@H:10]([CH3:32])[NH:11][C:12](=[O:31])[C@H:13]([CH3:30])[N:14]([C:16](=[O:29])[C@H:17]([CH:26]([CH3:28])[CH3:27])[NH:18]C(OC(C)(C)C)=O)[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:8][C:9](=[O:33])[C@H:10]([CH3:32])[NH:11][C:12](=[O:31])[C@H:13]([CH3:30])[N:14]([C:16](=[O:29])[C@H:17]([CH:26]([CH3:28])[CH3:27])[NH2:18])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 14673106Boc-L-Valyl-N-Mehtyl-L-Alanyl-L-Alanine Benzyl Ester

生成物 1

HCID 14673108L-Valyl-N-Methyl-L-Alanyl-L-Alanine Benzyl Ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-15 °C

実験手順

A stirred solution of 17 g (0.0367 mole) Boc-L-valyl-N-methyl-L-alanyl-L-alanine benzyl ester in 170 ml of dry dichloromethane was cooled at -10° C. as 85 ml of trifluoroacetic acid, previously cooled at -15° C., was added. After 16 hours -5° C., the reaction was carefully poured with good stirring into a mixture of 93 g of sodium bicarbonate, ice, and 250 ml of dichloromethane. The organic layer was separated and the aqueous layer was extracted with another 75 ml of dichloromethane. The combined organic layers were washed with 3×75 ml of saturated sodium bicarbonate solution, dried over magnesium sulfate, and evaporated to give 12.8 g (96% of theory) of crude product which was used in step 5 without further purification. FAB m.s. showed a molecular ion peak at 364.

後処理

  1. additionwas added
  2. additionAfter 16 hours -5° C., the reaction was carefully poured
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with another 75 ml of dichloromethane
  5. washThe combined organic layers were washed with 3×75 ml of saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customto give 12.8 g (96% of theory) of crude product which
  9. customwas used in step 5 without further purification

出典と根拠

ORDレコード
ord-b46877ae40a24e108619d0faeee63bf7
出典データセット
uspto-grants-1990_04
特許番号
US04914188

反応ノート

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