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

HRID 620039

反応式

HRID 620039 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e48ef4dda9a74b3489f5acecf41d1a4b
出典データセット
uspto-grants-1989_04
特許番号
US04818757

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