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

HRID 1625004ノート

反応式

HRID 1625004 の反応式
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]

参加物

6

反応物 5

HCID 679Dimethyl Sulfoxide2 回HCID 10340Sodium CarbonateHCID 24841Hydrogen iodideHCID 23668193Sodium NitriteHCID 59515825(R)-2-(5-Amino-1-oxoisoquinolin-2(1H)-yl)propyl acetate

生成物 1

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

実験手順

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

後処理

  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)

出典と根拠

ORDレコード
ord-1882d9c5f9fc480ba716ff280449d7bc
出典データセット
uspto-grants-2014_07
特許番号
US08779144B2

反応ノート

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