Benzyl chloroformate → Methyl 1-{[(benzyloxy)carbonyl]amino}cyclopropane-1-carboxylate

HRID 1366569

反応式

HRID 1366569 の反応式
[NH2:1][C:2]1([C:5]([O:7][CH3:8])=[O:6])[CH2:4][CH2:3]1.C([O-])(O)=O.[Na+].Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)Cl.O>[C:19]1([CH2:18][O:17][C:15]([NH:1][C:2]2([C:5]([O:7][CH3:8])=[O:6])[CH2:4][CH2:3]2)=[O:16])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

6

反応物 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 2735309Methyl 1-aminocyclopropanecarboxylate

生成物 1

HCID 13736078Methyl 1-{[(benzyloxy)carbonyl]amino}cyclopropane-1-carboxylate収率 46.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Methyl 1-aminocyclopropanecarboxylate (15.83 g, 104.43 mmol) was dissolved in a mixture of CH2Cl2 (150 mL) and water (150 mL). To this mixture was added NaHCO3 (35.09 g, 417.72 mmol) followed by benzyl chloroformate (15.43 mL, 109.64 mmol). The mixture was stirred vigorously for 2 hours, and after separation of the two layers, the aqueous layer was extracted with 100 mL of CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo to provide methyl 1-({[(phenylmethyl)oxy]carbonyl}amino)cyclopropanecarboxylate (12.0 g, 46%). LCMS: (M+H)+: 206.1.

後処理

  1. customafter separation of the two layers
  2. extractionthe aqueous layer was extracted with 100 mL of CH2Cl2
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-64e8950173aa4bb6b99e78a6907dcfa5
出典データセット
uspto-grants-2011_02
特許番号
US07893056B2

関連ノート

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