Toluene → 1-[[Methyl[(S)-3-[(4-morpholinylcarbonyl)amino]-2-oxo-4-phenylbutyl]amino]carbonyl]-L-proline, phenylmethyl ester

HRID 620039

반응식

HRID 620039 반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[N+](C1C=CC([O:14][C:15]([NH:17][C@@H:18]([CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:19](=[O:40])[CH2:20][N:21]([CH3:39])[C:22]([N:24]2[CH2:38][CH2:37][CH2:36][C@H:25]2[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[O:23])=O)=CC=1)([O-])=O.C1(C)C=CC=CC=1.N1CCC[C@H]1C(OCC1C=CC=CC=1)=O>C(OCC)(=O)C>[CH3:39][N:21]([CH2:20][C:19](=[O:40])[C@@H:18]([NH:17][C:15]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:14])[CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:22]([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:23]

참가 물질

6

반응물 4

HCID 1140TolueneHCID 8083MorpholineHCID 736155Benzyl L-prolinateHCID 141272261-[[[(S)-3-[[(4-nitrophenoxy)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester

생성물 1

HCID 144994961-[[Methyl[(S)-3-[(4-morpholinylcarbonyl)amino]-2-oxo-4-phenylbutyl]amino]carbonyl]-L-proline, phenylmethyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

Morpholine (1 ml., 11.4 mmole) is added to a stirring solution of 1-[[[(S)-3-[[(4-nitrophenoxy)carbonyl]amino]-2-oxo-4-phenylbutyl]methylamino]carbonyl]-L-proline, phenylmethyl ester (0.9 g., 1.58 mmole) ih toluene at 0° in one portion. The reaction mixture turns yellow in 15 minutes and TLC indicates complete loss of starting material after 30 minutes. The resulting solution is washed sequentially with water, 1N hydrochloric acid, and 10% sodium bicarbonate. The organic layer is dried (MgSO4) and concentrated. The crude product is purified by preparative layer chromatography to give 0.26 g. of 1-[[methyl[(S)-3-[(4-morpholinylcarbonyl)amino]carbonyl]-2-oxo-4-phenylbutyl]amino]carbonyl]L-proline, phenylmethyl ester as a yellow oil. TLC (ethyl acetate) Rf =0.18.

후처리

  1. waitTLC indicates complete loss of starting material after 30 minutes
  2. washThe resulting solution is washed sequentially with water, 1N hydrochloric acid, and 10% sodium bicarbonate
  3. dry with materialThe organic layer is dried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product is purified by preparative layer chromatography
  6. customto give 0.26 g

출처 및 근거

ORD 기록
ord-e48ef4dda9a74b3489f5acecf41d1a4b
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04818757

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