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

HRID 2254526노트

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HRID 2254526 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 14673104N-Methyl-L-Alanyl-L-Alanine benzyl Ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-10 °C

실험 절차

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 mangesium sulfate, and evaporated to give 11.6 g (91% of theory) of crude product which was used in step 3 without further purification.

후처리

  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 mangesium 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

출처 및 근거

ORD 기록
ord-9cd9226e46a0475ebf8ee0d0a4e851df
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05236899

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