Trifluoroacetic acid → N-Methyl-L-Alanyl-L-Alanine benzyl Ester

HRID 2072755ノート

反応式

HRID 2072755 の反応式
[CH2:1]([O:8][C:9](=[O:26])[C@H:10]([CH3:25])[NH:11][C:12](=[O:24])[C@H:13]([CH3:23])[N:14](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:26])[C@H:10]([CH3:25])[NH:11][C:12](=[O:24])[C@H:13]([CH3:23])[NH:14][CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 14673102Benzyl (S)-2-[(S)-2-(tert-butoxycarbonyl-methyl-amino)-propanoylamino]-propionate

生成物 1

HCID 14673104N-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
-10 °C

実験手順

To a stirred solution of 17 g (0.0466 mole) of Boc-N-methyl-L-alanyl-L-alanine benzyl ester in 150 ml of dry dichloromethane, cooled at -10° C., was added 100 ml trifluoroacetic acid, which was previously cooled at -10° C. The reaction mixture was stirred for 16 hours at -5° C., then poured carefully with good stirring into a mixture of 177 g of sodium bicarbonate, ice, and 150 ml of dichloromethane. The organic layer was separated and the aqueous layer was further extracted with another 60 ml of dichloromethane. The combined organic layers were washed with 3×50 ml of saturated sodium bicarbonate solution, dried over manesium sulfate, and evaporated to give 11.6 g (91% of theory) of crude product which was used in step 3 without further purification.

後処理

  1. additionpoured carefully
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was further extracted with another 60 ml of dichloromethane
  4. washThe combined organic layers were washed with 3×50 ml of saturated sodium bicarbonate solution
  5. dry with materialdried over manesium sulfate
  6. customevaporated
  7. customto give 11.6 g (91% of theory) of crude product which
  8. customwas used in step 3 without further purification

出典と根拠

ORDレコード
ord-9d11f8451d2b4cf59e56b9c9ca5c76c8
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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