tert-Butanol → Ethyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate

HRID 1436375

反応式

HRID 1436375 の反応式
C([N:3]([CH2:6]C)CC)C.[CH2:8]([O:10][C:11]([C:13]1(C(O)=O)[CH2:15][CH2:14]1)=[O:12])[CH3:9].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.[C:36]([OH:40])([CH3:39])([CH3:38])[CH3:37]>>[CH2:8]([O:10][C:11]([C:13]1([NH:3][C:6]([O:40][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:26])[CH2:14][CH2:15]1)=[O:12])[CH3:9]

参加物

5

反応物 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 117894721-(Ethoxycarbonyl)cyclopropanecarboxylic acid

生成物 1

HCID 10242916Ethyl 1-((tert-butoxycarbonyl)amino)cyclopropanecarboxylate収率 91%

実験手順

Triethylamine (29.82 mL, 214 mmol) was added under nitrogen dropwise to a mixture of 1,1-cyclopropanedicarboxylic acid monoethyl ester (31.518 g, 199 mmol), prepared in the previous step, and diphenylphosphoryl azide (47.4 mL, 219 mmol) in 40 mL of tert-butanol at room temperature. After the addition, the reaction was refluxed for 5 h. The reaction was concentrated under reduced pressure. The residue was taken up in ethyl acetate and extracted three times each with 5% citric acid, saturated NaHCO3 and saturated NaCl. The ethyl acetate layer was dried (anhydrous MgSO4), filtered and the solvent removed under reduced pressure to give 1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclopropane carboxylic acid ethyl ester (41.3931 g, 91%) as a yellow oil, MS (ES) m/z 130.0 [M+H-tBoc].

後処理

  1. additionAfter the addition
  2. temperaturethe reaction was refluxed for 5 h
  3. concentrationThe reaction was concentrated under reduced pressure
  4. extractionextracted three times each with 5% citric acid, saturated NaHCO3 and saturated NaCl
  5. dry with materialThe ethyl acetate layer was dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

出典と根拠

ORDレコード
ord-2ed34a90c5f0453b9150e0fa309f4594
出典データセット
uspto-grants-2009_11
特許番号
US07618990B2

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