Hydrochloric Acid → 3-Ethyl-5-(1H-indol-3-ylmethyl)-imidazolidine-2,4-dione

HRID 1725832노트

반응식

HRID 1725832 반응식
Cl.CO[C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[CH2:25]([N:27]=[C:28]=[O:29])[CH3:26].Cl>ClCCl.O1CCOCC1>[CH2:25]([N:27]1[C:4](=[O:17])[CH:5]([CH2:7][C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][CH:9]=2)[NH:6][C:28]1=[O:29])[CH3:26]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 2734891Methyl tryptophanate hydrochloride

생성물 1

HCID 138140423-Ethyl-5-(1H-indol-3-ylmethyl)-imidazolidine-2,4-dione수율 93.3%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

To a solution of L-tryptophan methyl ester hydrochloride (0.510 mg, 0.002 mol.) in dichloromethane (10 mL) was added triethyl amine (0.350 mL, 0.0025 mol.) followed by ethylisocyanate (0.198 mL, 0.0025 mol.). The reaction mixture was stirred at room temperature for 24 hr, and then concentrated. The residue obtained was diluted with dioxane (10 mL) and then conc. HCl (5 mL) was added. The mixture was heated at reflux for 3-4 hr. The reaction mixture was extracted in ethyl acetate, washed with water, dried and concentrated. The residue was purified by column chromatography on silica gel using 60% ethyl acetate-hexane to give 893-04 (480 mg, 93%): mp 167-170° C. (lit. 163-164° C.), 1H NMR (400 MHz, CDCl3): 0.99 (t, J=6.8 Hz, 3H), 2.95-3.01 (dd, J=8.4 and 14.8 Hz, 1H), 3.34-3.46 (m, 3H), 4.19-4.22 (dd, J=3.6 and 8.8 Hz, 1H), 5.70 (s, 1H), 6.98 (d, J=2.0 Hz, 1H), 7.06-7.10(dd, J=8.0 and 6.8 Hz, 1H), 7.16(dd, J=7.2 and 6.8 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.55 (d, J=8.8 Hz, 1H), 8,18 (s, 1H).

후처리

  1. concentrationconcentrated
  2. customThe residue obtained
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 3-4 hr
  5. extractionThe reaction mixture was extracted in ethyl acetate
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel using 60% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-1e90f973de974d2fa5fcb08a2d3f7d1c
출처 데이터셋
uspto-grants-2009_02
특허 번호
US07491743B2

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