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

HRID 1366569

반응식

HRID 1366569 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-64e8950173aa4bb6b99e78a6907dcfa5
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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