Benzyl chloroformate → (1-Cyano-2-cyclopropyl-1-methyl-ethyl)-carbamic acid benzyl ester

HRID 1480124

반응식

HRID 1480124 반응식
[NH2:1][C:2]([CH3:9])([CH2:5][CH:6]1[CH2:8][CH2:7]1)[C:3]#[N:4].CCN(C(C)C)C(C)C.[C:19](Cl)(=[O:28])[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:20][C:19](=[O:28])[NH:1][C:2]([C:3]#[N:4])([CH3:9])[CH2:5][CH:6]1[CH2:8][CH2:7]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 847160492-Amino-3-cyclopropyl-2-methyl-propionitrile

생성물 1

HCID 90204034(1-Cyano-2-cyclopropyl-1-methyl-ethyl)-carbamic acid benzyl ester수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
45 °C

실험 절차

To a solution of 2-Amino-3-cyclopropyl-2-methyl-propionitrile (Example 66a, 5.01 g, 30.9 mmol) in dry THF (119 mL) was added DIEA (12.1 mL, 67.9 mmol) and benzyl carbonochloridate (CAN 501-53-1, 5.57 mL, 37.1 mmol). The reaction was stirred at 45° C. for 18 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethylacetate and extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography eluting with a gradient of heptane/ethylacetate to yield the title compound (6.2, 60%) as a colorless oil. MS (ESI, m/z): 259.5 (M+H+).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethylacetate
  3. extractionextracted with an 1.0M aqueous solution of sodium bicarbonate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customevaporated down to dryness
  6. customThe crude material was purified by flash chromatography
  7. washeluting with a gradient of heptane/ethylacetate

출처 및 근거

ORD 기록
ord-05123ffb9a4543f9a9175e88a87b33c5
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409866B2

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