Methanol → methyl 2-(5-methoxy-1H-indol-3-yl)acetate

HRID 527441

반응식

HRID 527441 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([OH:15])=[O:14].[CH2:16]1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(N(CC)CC)C.CO>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][C:13]([O:15][CH3:16])=[O:14]

참가 물질

6

반응물 4

HCID 887MethanolHCID 8471TriethylamineHCID 189865-Methoxyindoleacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chloride

생성물 1

HCID 594955methyl 2-(5-methoxy-1H-indol-3-yl)acetate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A reaction mixture containing 2-(5-methoxy-1H-indol-3-yl)acetic acid (0.5 g, 2.44 mmol) and BOP-Cl (0.62 g, 2.44 mmol) in 7 mL of anhydrous CH2Cl2 was treated with triethyl amine (0.49 g, 4.87 mmol) and allowed to stir at ambient temperature for 5 min. The mixture was then combined with anhydrous methanol (0.34 mL) and continuously stirred overnight at room temperature. Following dilution with dichloromethane (30 mL), the organic solution was washed with water (2×15 mL), dried over Na2SO4, and filtered (using a commercial phase separator syringe with attached drying cartridge). The organic filtrate was collected and concentrated in vacuo and the crude ester was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to afford the title compound as viscous yellow oil, which permanently crystallized upon storage at −20° C. (453 mg, 85%). C12H13NO3, Mr=219.24; 1H NMR (400 MHz, DMSO-d6) d: 3.60 (s, 3H), 3.70 (s, 2H), 3.74 (s, 3H), 6.72 (dd, J=2.4/8.8 Hz, 1H), 6.96 (d, J=2.4 Hz, 1H), 7.19 (d, J=2.4 Hz, 1H), 7.23 (d, J=8.8 Hz, 1H), 10.77 (s, 1H); LCMS (ESI) tR: 1.95 min (>99%, UV254), m/z: 220.1 [M+1]+.

후처리

  1. washthe organic solution was washed with water (2×15 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered (using a commercial phase separator syringe with attached drying cartridge)
  4. customThe organic filtrate was collected
  5. concentrationconcentrated in vacuo
  6. customthe crude ester was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient)

출처 및 근거

ORD 기록
ord-204a741038444dafb862da515d2aac5e
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346803B2

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