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Dimethylformamide → Benzyl 3-[(tert-butoxycarbonyl)(n-propyl)amino]azetidine-1-carboxylate

HRID 1425373
ノート
印刷プレビュー

反応式

HRID 1425373 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][N:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:25](I)[CH2:26][CH3:27].CN(C=O)C>C1COCC1.O>[C:1]([O:5][C:6]([N:8]([CH2:25][CH2:26][CH3:27])[CH:9]1[CH2:10][N:11]([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 67548302Benzyl 3-{[(tert-butoxy)carbonyl]amino}azetidine-1-carboxylate

生成物 1

HCID 67548639Benzyl 3-[(tert-butoxycarbonyl)(n-propyl)amino]azetidine-1-carboxylate収率 93%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of benzyl 3-[(tert-butoxycarbonyl)amino]azetidine-1-carboxylate obtained in Example (227a) (472 mg, 1.54 mmol) in THF (5 mL) was added to a suspension of sodium hydride (55%) (134 mg, 3.08 mmol) in THF (10 mL) at 0° C. Subsequently, propyl iodide (0.75 mL, 7.70 mmol) was added at 0° C., and the mixture was stirred at room temperature for 70 minutes. THF (4 mL) and DMF (5 mL) were added, followed by further stirring for 18 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. Thereafter, the combined organic layers were washed with brine and dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1) to obtain 499 mg of the title compound as a colorless oily substance (93%).

後処理

  1. stirringby further stirring for 18 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThereafter, the combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-0db74ed893644ab4a1c95a5954ee70d8
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927588B2

反応ノート

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