Benzyl chloroformate → benzyl N-(1-cyano-1-methylbutyl)carbamate

HRID 1486243노트

반응식

HRID 1486243 반응식
[NH2:1][C:2]([CH3:8])([CH2:5][CH2:6][CH3:7])[C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1.O>[C:3]([C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([CH2:5][CH2:6][CH3:7])[CH3:8])#[N:4]

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 208880Pentanenitrile, 2-amino-2-methyl-

생성물 1

HCID 117861119benzyl N-(1-cyano-1-methylbutyl)carbamate수율 99.8%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

20 g (178.3 mmol) of rac-2-amino-2-methylpentanonitrile (described in: Deng, S L. et al., Synthesis 2001, 2445-2449; Freifelder, M. et al., J. Am. Chem. Soc. 1960, 696-698) were initially charged in 2.63 l of THF/water (8/1), and 76.4 g (552.7 mmol) of potassium carbonate were added. Then 27.6 ml (196.1 mmol) of benzyl chloroformate were slowly added dropwise at 0° C. and the mixture was stirred at RT overnight. The reaction mixture was concentrated, and the residue was admixed with water and extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated. The residue was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate=4/1). 43.84 g of the target compound were obtained (76% of theory, 76% purity).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by means of silica gel chromatography (eluent:cyclohexane/ethyl acetate=4/1)

출처 및 근거

ORD 기록
ord-3d8858066dc04594ab0fef1838963295
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09422285B2

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