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4-Methylmorpholine → Isopropyl (2RS,3S)-3-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-2-hydroxy-4-phenylbutyrate

HRID 1061681
ノート
印刷プレビュー

反応式

HRID 1061681 の反応式
CN1CCOCC1.ON1C2C=CC=CC=2N=N1.[NH2:18][C@@H:19]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH:20]([OH:27])[C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22].[C:35]([N:38]1[CH:43]=[C:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:41]([CH2:50][C:51](O)=[O:52])[C:40](=[O:54])[CH:39]1[CH:55]([CH3:57])[CH3:56])(=[O:37])[CH3:36].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(OCC)(=O)C>[C:35]([N:38]1[CH:43]=[C:42]([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:41]([CH2:50][C:51]([NH:18][C@@H:19]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:20]([OH:27])[C:21]([O:23][CH:24]([CH3:25])[CH3:26])=[O:22])=[O:52])[C:40](=[O:54])[CH:39]1[CH:55]([CH3:57])[CH3:56])(=[O:37])[CH3:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11736536isopropyl (2RS,3S)-3-amino-2-hydroxy-4-phenylbutyrateHCID 22284314{(3RS)-4-Acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetic acid

生成物 1

HCID 60073851
Isopropyl (2RS,3S)-3-{(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}methylcarbonylamino-2-hydroxy-4-phenylbutyrate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

N-Methylmorpholine (67 μl), 1-hydroxybenzotriazole (103 mg) and isopropyl (2RS,3S)-3-amino-2-hydroxy-4-phenylbutyrate (144 mg, Reference compound No. 4-1) are added to a solution of {(3RS)-4-acetyl-3-isopropyl-2-oxo-6-phenyl-1,2,3,4-tetrahydropyrazin-1-yl}acetic acid (160 mg, Reference compound No. 51-1) in methylene chloride (5 ml). The mixture is cooled with ice, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (116 mg) is added to the mixture, and the whole is stirred overnight. Ethyl acetate is added to the reaction mixture, the whole is washed with a 0.1 N aqueous sodium hydroxide solution, saturated brine, 0.1 N hydrochloric acid and saturated brine successively, and the organic layer is dried over anhydrous magnesium sulfate. The organic layer is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography to give the titled compound (259 mg).

後処理

  1. additionis added to the mixture
  2. washthe whole is washed with a 0.1 N aqueous sodium hydroxide solution, saturated brine, 0.1 N hydrochloric acid and saturated brine successively
  3. dry with materialthe organic layer is dried over anhydrous magnesium sulfate
  4. concentrationThe organic layer is concentrated under reduced pressure
  5. customthe resulting residue is purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-25d5381d77034c43927a7eae10684b87
出典データセット
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06960575B2

反応ノート

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