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

HRID 1480124

反応式

HRID 1480124 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-05123ffb9a4543f9a9175e88a87b33c5
出典データセット
uspto-grants-2016_08
特許番号
US09409866B2

関連ノート

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