1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → dibenzylphosphoryl-L-alanyl-L-prolyl-L-phenylalanine ethylester

HRID 280770

반응식

HRID 280770 반응식
[CH2:1]([P:8]([NH:17][C@H:18]([C:20]([N:22]1[CH2:29][CH2:28][CH2:27][C@H:23]1[C:24](O)=[O:25])=[O:21])[CH3:19])([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:41]([O:43][C:44](=[O:54])[C@H:45]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[NH2:46])[CH3:42].CCN=C=NCCCN(C)C>CN(C=O)C.C(OCC)(=O)C>[CH2:41]([O:43][C:44](=[O:54])[C@H:45]([CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[NH:46][C:24](=[O:25])[C@@H:23]1[CH2:27][CH2:28][CH2:29][N:22]1[C:20](=[O:21])[C@H:18]([CH3:19])[NH:17][P:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9])[CH3:42]

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 53804723Dibenzylphosphory-L-alanyl-L-proline

생성물 1

HCID 70042340dibenzylphosphoryl-L-alanyl-L-prolyl-L-phenylalanine ethylester수율 76.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
-15 °C

실험 절차

Dibenzylphosphoryl-L-alanyl-L-proline (1.2 g, 2.5 m mole), HOBt (338 mg, 2.5 m mole) and L-phenylalanine ethylester hydrochloride (690 mg, 3 m mole) were suspended in DMF (10 ml) and WSC (0.5 ml) were added thereto while cooling to -15° C. and stirring. The reaction was carried out for 3 hours under cooling and then overnight at room temperature. To the reaction solution, ethyl acetate (100 ml) was added, and the mixture was washed with 1N hydrochloric acid and water in order, and dried with anhydrous sodium sulfate. The the dried solution was distilled under reduced pressure to obtain an oily dibenzylphosphoryl-L-alanyl-L-prolyl-L-phenylalanine ethylester material (1.3 g). The oily material gave a single spot with Rf 0.7 by thin layer chromatography (developing solvent; chloroform:methanol:acetic acid=95:5:3, colour forming method: spraying for 25% hydrobromic acid and 0.1% ninhydrine, and heating).

후처리

  1. temperatureunder cooling
  2. customovernight
  3. customat room temperature
  4. washthe mixture was washed with 1N hydrochloric acid and water in order
  5. dry with materialdried with anhydrous sodium sulfate
  6. distillationThe the dried solution was distilled under reduced pressure

출처 및 근거

ORD 기록
ord-f2a8ad9e6139456f9120742602b8cd00
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04590178

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