Ammonia → Meconin

HRID 336812

반응식

HRID 336812 반응식
CN1[C@@H]([C@H:12]2[O:21][C:19](=[O:20])[C:18]3[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=[CH:14][C:13]2=3)C2C(OC)=C3OCOC3=CC=2CC1.N1C=CC=CC=1.ICl.N>C(#N)C>[CH3:25][O:24][C:16]1[C:17]([O:22][CH3:23])=[C:18]2[C:13]([CH2:12][O:21][C:19]2=[O:20])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 275196Noscapine2회HCID 10220417Pyridine Iodine Monochloride

생성물 1

HCID 68437Meconin수율 76%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Iodination of noscapine was now carried out by addition of pyridine-iodine chloride (1.46 g, 6 mmol) to a solution of noscapine (1 g, 2.42 mmol) in acetonitrile (20 ml) and the resultant mixture was stirred at room temperature for 6 hours and then at 100° C. for 6 hours. After cooling, excess ammonia was added and filtered through celite pad to remove the black nitrogen triiodide. The filtrate was made acidic with 1 M HCl and filtered to collect the yellow solid, washed with water and air-dried to afford (S)-3-(R)-9-iodo-4-methoxy-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)-6,7-dimethoxyisobenzofuran-1 (3H)-one (5). Yield: 76%, mp 172.3-172.6° C.; 1H NMR (CDCl3, 400 MHz): δ 7.15 (d, 1H, J=8.1 Hz), 7.01 (d, 1H, J=8.1 Hz), 6.11 (s, 2H), 5.36 (d, 1H, J=4.8 Hz), 4.25 (d, 1H, J=4.8 Hz), 3.85 (s, 3H), 3.74 (s, 3H), 3.72 (s, 3H), 2.78-2.72 (m, 2H), 2.55-2.50 (m, 2H), 2.32 (s, 3H); 13C NMR (CDCl3, 100 MHz): δ 168.2, 155.1, 151.5, 148.3, 146.5, 143.1, 140.3, 120.4, 119.5, 113.3, 101.5, 85.9, 82.2, 61.8, 56.6, 55.7, 54.5, 54.1, 51.2, 39.8, 30.1, 18.8; HRMS (ESI): m/z Calcd. for C22H23INO7 (M+1), 540.3209. Found, 540.3227 (M+1).

후처리

  1. temperatureAfter cooling
  2. filtrationfiltered through celite pad
  3. customto remove the black nitrogen triiodide
  4. filtrationfiltered
  5. customto collect the yellow solid
  6. washwashed with water
  7. customair-dried

출처 및 근거

ORD 기록
ord-a1ecc9294f534234925404d345b797fa
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889705B2

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