Benzoyl chloride → N-benzoyl-L-alanyl-L-proline ethylamide

HRID 47045노트

반응식

HRID 47045 반응식
Br.[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].[OH-].[Na+].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:3]

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 14798Sodium Hydroxide2회HCID 70602162L-alanyl-L-proline ethylamide hydrobromide

생성물 1

HCID 54309979N-benzoyl-L-alanyl-L-proline ethylamide수율 68.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1.42 g (0.0048 mol) of L-alanyl-L-proline ethylamide hydrobromide were dissolved in 20 ml of methylene chloride, 21.8 ml (0.01 mol) of 0.5-N sodium hydroxide solution were added followed by 0.54 ml (0.0053 mol) of benzoyl chloride. The mixture was stirred vigorously at room temperature for 1 hour with care being taken that the solution remained basic, this being achieved by the addition of a few drops of 0.5-N sodium hydroxide solution. The layers were then allowed to separate and the methylene chloride layer was separated, dried over magnesium sulphate and evaporated to an oil which crystallised on treatment with ethyl acetate. The crystals were filtered off, washed and dried to yield 1.05 g of N-benzoyl-L-alanyl-L-proline ethylamide of melting point 200°-202° C.; [α]D20 =-82.7° (c=0.99 in methanol).

후처리

  1. customto separate
  2. customthe methylene chloride layer was separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated to an oil which
  5. customcrystallised on treatment with ethyl acetate
  6. filtrationThe crystals were filtered off
  7. washwashed
  8. customdried

출처 및 근거

ORD 기록
ord-00cb2a1f19a44f2d8f439eb07dc5a70f
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04176116

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