Perchloric Acid → HCID 66603844、化合物

HRID 2406372ノート

反応式

HRID 2406372 の反応式
[OH:1][CH:2]([C:7]1[C:8]([I:21])=[C:9]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4].Cl(O)(=O)(=O)=O.C(=O)([O-])O.[Na+]>C(OC(C)(C)C)(=O)C>[C:7]([O:1][CH:2]([C:7]1[C:8]([I:21])=[C:9]2[C:16]3[CH2:17][CH2:18][CH2:19][CH2:20][C:15]=3[S:14][C:10]2=[N:11][C:12]=1[CH3:13])[C:3]([O:5][CH3:6])=[O:4])([CH3:8])([CH3:12])[CH3:2]

参加物

5

反応物 3

HCID 24247Perchloric AcidHCID 516892Sodium BicarbonateHCID 66603698Methyl hydroxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate

生成物 1

HCID 66603844HCID 66603844、化合物収率 38%

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

実験手順

A suspension of methyl hydroxy(4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)acetate (Preparation 9, 10.0 g, 23.97 mmol) in tert-butyl acetate (250 mL) was stirred vigorously for 5 minutes prior to the dropwise addition of perchloric acid (70%, 6.15 mL, 71.90 mmol). The resulting mixture was stirred at room temperature for 20 minutes. The mixture was neutralised by addition of a saturated aqueous sodium hydrogen carbonate solution (60 mL) and extracted with ethyl acetate (250 mL). The layers were separated and the aqueous layer was further extracted with ethyl acetate (250 mL). The combined organic layers were washed with brine (250 mL), dried over MgSO4 and concentrated in vacuo to yield the crude product. The residue was purified by flash column chromatography eluting with ethyl acetate/heptane (10-40%) to give the title compound, 4.26 g, in a 38% yield. 1H NMR (400 MHz, CDCl3) δ ppm 1.23 (s, 9H), 1.81-1.92 (m, 4H), 2.66 (s, 3H), 2.79-2.89 (m, 2H), 3.21-3.27 (m, 2H), 3.68 (s, 3H), 5.95 (s, 1H).

後処理

  1. stirringThe resulting mixture was stirred at room temperature for 20 minutes
  2. extractionextracted with ethyl acetate (250 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was further extracted with ethyl acetate (250 mL)
  5. washThe combined organic layers were washed with brine (250 mL)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customto yield the crude product
  9. customThe residue was purified by flash column chromatography
  10. washeluting with ethyl acetate/heptane (10-40%)

出典と根拠

ORDレコード
ord-97ff9ffa227b459e8e6498dc1fa82c35
出典データセット
uspto-grants-2014_08
特許番号
US08809363B2

反応ノート

読み込み中…