Sulfuric Acid → HCID 69672858, 화합물

HRID 63937노트

반응식

HRID 63937 반응식
[CH2:1]([O:3][C:4](=[O:22])[CH:5]([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])[OH:6])[CH3:2].C(O[C:27]([CH3:30])([CH3:29])[CH3:28])(=O)C.S(=O)(=O)(O)O>ClCCl>[CH2:1]([O:3][C:4](=[O:22])[CH:5]([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])[O:6][C:27]([CH3:30])([CH3:29])[CH3:28])[CH3:2]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 10908tert-Butyl acetateHCID 67606534HCID 67606534, 화합물

생성물 1

HCID 69672858HCID 69672858, 화합물수율 36%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Ethyl-2-[4-iodo-2-methyl-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridine-3-yl]-2-hydroxyacetate (3 g, 7 mmol) was taken up in 20 mL dichloromethane and tert-butyl acetate (20 mL, 170 mmol) and the mixture coiled to 3° C. in an ice/water bath. Concentrated sulphuric acid (1.14 mL, 21 mmol) was then added dropwise and the mixture allowed to warm to room temperature over 3 hours. The reaction was quenched by the addition of 100 mL of 1M NaOH and 100 mL water and the organic layer separated. The organics were washed with brine (100 mL), dried over MgSO4 and evaporated under reduced pressure. The residue was purified by flash chrmoatography using a gradient of EtOAc in heptane as eluant (0:100 to 30:70) to afford the title compound as a white solid (1.22 g, 36%). 1H NMR (400 MHz, CDCl3) δ 1.20 (t, 3H), 1.23 (s, 9H), 1.81-1.94 (m, 4H), 2.66 (s, 3H), 2.80-2.87 (m, 2H), 3.22-3.31 (m, 2H), 4.10-4.22 (m, 2H), 5.90 (s, 1H).

후처리

  1. customThe reaction was quenched by the addition of 100 mL of 1M NaOH and 100 mL water
  2. customthe organic layer separated
  3. washThe organics were washed with brine (100 mL)
  4. dry with materialdried over MgSO4
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chrmoatography

출처 및 근거

ORD 기록
ord-e3b27a76eb3944ae9e7ac2b1ce9f8274
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447116B2

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