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4-Methylmorpholine → N-[3-(3-pyridyl)propanoyl]-L-valyl-N-[3,3,4,4,5,5,5-heptafluoro-1-(1-methylethyl)-2-oxopentyl]-L-prolinamide

HRID 613240
ノート
印刷プレビュー

反応式

HRID 613240 の反応式
[NH2:1][C@H:2]([C:6]([N:8]1[CH2:31][CH2:30][CH2:29][C@H:9]1[C:10]([NH:12][C@H:13]([C:17]([C:19]([C:22]([C:25]([F:28])([F:27])[F:26])([F:24])[F:23])([F:21])[F:20])=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])=[O:7])[CH:3]([CH3:5])[CH3:4].Cl.CN1CCOCC1.[N:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][CH2:47][C:48](Cl)=[O:49])[CH:41]=1>C(Cl)Cl>[N:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][CH2:47][C:48]([NH:1][C@H:2]([C:6]([N:8]2[CH2:31][CH2:30][CH2:29][C@H:9]2[C:10]([NH:12][CH:13]([CH:14]([CH3:15])[CH3:16])[C:17](=[O:18])[C:19]([F:20])([F:21])[C:22]([F:23])([F:24])[C:25]([F:28])([F:26])[F:27])=[O:11])=[O:7])[CH:3]([CH3:4])[CH3:5])=[O:49])[CH:41]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 149870663-Pyridin-3-ylpropanoyl chlorideHCID 131721523H-Val-Pro-Val-CF2CF2CF3.hydrochloride

生成物 1

HCID 88297363N-[3-(3-pyridyl)propanoyl]-L-valyl-N-[3,3,4,4,5,5,5-heptafluoro-1-(1-methylethyl)-2-oxopentyl]-L-prolinamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-20 °C

実験手順

Dissolve H-Val-Pro-Val-CF2CF2CF3.hydrochloride (185 mg, 0.37 mmol) in methylene chloride (10 mL) and cool to -20° C. while stirring. Add N-methylmorpholine (0.2 mL, 2.0 mmol) and immediately follow with a dropwise addition of 3-(3-pyridyl)propanoyl chloride in methylene chloride (5 mL) at such a rate as to maintain the internal reaction temperature at -10° C. or less. After completion of the addition, allow the reaction mixture to warm to room temperature. After 1.5 hours at room temperature, dilute the reaction mixture with methylene chloride (20 mL) and wash with 1N HCl (2×20 mL), saturated NaHCO3 (2×20 mL) and brine (1×20 mL). Dry (MgSO4) and concentrate in vacuo to give the title product in crude form. Immediately purify the crude product by flash chromatograpy (2×15 cm column eluted with 1:27 MeOH--CH2Cl2) to give the title compound.

後処理

  1. temperatureto maintain the internal reaction temperature at -10° C. or less
  2. additionAfter completion of the addition
  3. temperatureto warm to room temperature
  4. washwash with 1N HCl (2×20 mL), saturated NaHCO3 (2×20 mL) and brine (1×20 mL)
  5. dry with materialDry (MgSO4)
  6. concentrationconcentrate in vacuo

出典と根拠

ORDレコード
ord-d84e4093cbf54a42bc40b88bca162bfc
出典データセット
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06008196

反応ノート

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