Dimethyl Sulfoxide → (R)-2-(5-Iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

HRID 1625004노트

반응식

HRID 1625004 반응식
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])[C:7]2=[O:12].N([O-])=O.[Na+].CS(C)=O.[IH:28].C([O-])([O-])=O.[Na+].[Na+]>>[I:28][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]([C@H:13]([CH3:19])[CH2:14][O:15][C:16](=[O:18])[CH3:17])[C:7]2=[O:12]

참가 물질

6

반응물 5

HCID 679Dimethyl Sulfoxide2회HCID 10340Sodium CarbonateHCID 24841Hydrogen iodideHCID 23668193Sodium NitriteHCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

생성물 1

HCID 67203267(R)-2-(5-Iodo-1-oxoisoquinolin-2(1H)-yl)propyl acetate

실험 절차

Acetic acid (R)-2-(5-amino-1-oxo-1H-isoquinolin-2-yl)-propyl ester (790 mg, 0.0030 mol) was added to a solution of sodium nitrite (800 mg, 0.01 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) at room temperature. Aqueous hydrogen iodide (4 mL, 0.03 mol) in dimethyl sulfoxide (10 mL, 0.1 mol) was added. The reaction mixture was stirred at room temperature for 1 hour. The cooled reaction mixture was neutralized with saturated aq. Na2CO3 and extracted with methylene chloride (3×100 mL). The combined methylene chloride extracts were washed with brine and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed on 40 of silica gel column (0-50% EtOAc/Hexane) to give the desired product as a brown oil. MS m/z (M+H) 371.9

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted with methylene chloride (3×100 mL)
  3. washThe combined methylene chloride extracts were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was chromatographed on 40 of silica gel column (0-50% EtOAc/Hexane)

출처 및 근거

ORD 기록
ord-1882d9c5f9fc480ba716ff280449d7bc
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08779144B2

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