Pyridine → 1-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

HRID 522361

반응식

HRID 522361 반응식
[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[OH:9])[CH2:2][CH2:3][CH:4]=[CH2:5].N1C=CC=CC=1.[CH2:16]1[C:21](=[O:22])[N:20]([O:23][C:24](ON2C(=O)CCC2=O)=[O:25])[C:18](=[O:19])[CH2:17]1>C(#N)C.CN(C1C=CN=CC=1)C.CCOCC>[CH2:1]([C@@H:6]1[CH2:8][C@H:7]1[O:9][C:24]([O:23][N:20]1[C:21](=[O:22])[CH2:16][CH2:17][C:18]1=[O:19])=[O:25])[CH2:2][CH2:3][C:4]#[CH:5]

참가 물질

7

반응물 3

HCID 1049PyridineHCID 676246Di(succinimido) carbonateHCID 67304189rel-(1R,2R)-2-(pent-4-en-1-yl)cyclopropan-1-ol

생성물 1

HCID 895908351-[({[(1R,2R)-2-(pent-4-yn-1-yl)cyclopropyl]oxy}carbonyl)oxy]pyrrolidine-2,5-dione

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매HCID 6342Acetonitrile용매

반응 조건

온도
40 °C

실험 절차

To a solution of (1R,2R)-2-(pent-4-en-1-yl)cyclopropanol (See International Patent Application Publication No. WO08/057209) (2.13 g; 70% wt) in acetonitrile (20 ml) was added pyridine (1.5 ml), followed by N,N′-disuccinimidyl carbonate (3.74 g) and a crystal of DMAP. The mixture was stirred at 40° C. overnight. After cooling to room temperature, the reaction mixture was diluted with ether and washed with HCl 1N, water and brine and dried over sodium sulfate. The organic layer was filtered and concentrated to provide the desired product (2.88 g) as an oil. 1H NMR (500 MHz, CDCl3): δ (ppm) 4.06-4.03 (m, 1H), 2.87 (s, 4H), 2.28-2.25 (m, 2H), 1.98-1.97 (m, 1H), 1.72-1.65 (m, 2H), 1.46-1.40 (m, 2H), 1.31-1.24 (m, 1H), 1.12-1.08 (m, 1H), 0.72-0.68 (m, 1H).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with HCl 1N, water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was filtered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a462f20ee0eb40e099a1e0ec74193af1
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09328138B2

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