Hydrochloric Acid → Diethyl(2-((tert-butoxycarbonyl)amino)ethyl)(cyclopropyl)malonate

HRID 714920

反応式

HRID 714920 の反応式
[CH:1]1([CH:4]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[H-].[Na+].O1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])S1(=O)=O.Cl>CN(C)C=O>[CH2:13]([O:12][C:10](=[O:11])[C:4]([CH2:21][CH2:20][NH:19][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([CH:1]1[CH2:3][CH2:2]1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:14]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 127044081,3-Diethyl 2-cyclopropylpropanedioateHCID 235840203-Boc-1,2,3-oxathiazolidine 2,2-dioxide

生成物 1

HCID 117974976Diethyl(2-((tert-butoxycarbonyl)amino)ethyl)(cyclopropyl)malonate収率 50.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of diethyl cyclopropylmalonate (7.7 g) obtained in Step A of Example 388 in N,N-dimethylformamide (90 mL) was added sodium hydride (60% in mineral oil, 1.8 g), and the mixture was stirred at 0° C. for 30 min. To the reaction mixture was added tert-butyl 1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide (9.4 g) at the same temperature, and the mixture was stirred at 0° C. for 2 hr. To the reaction mixture was added 1M hydrochloric acid, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (6.7 g).

後処理

  1. stirringthe mixture was stirred at 0° C. for 2 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-5794d271586e43f4bd5ee8e6613b8f76
出典データセット
uspto-grants-2015_11
特許番号
US09187453B2

関連ノート

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