Hydrochloric Acid → 1-Adamantan-2-yl-4-benzyl-5-isopropyl-1,3-dihydro-imidazol-2-one

HRID 1092316노트

반응식

HRID 1092316 반응식
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([NH:14][CH:15]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16](=O)[CH:17]([CH3:19])[CH3:18])=[O:13])[CH2:8]2.Cl.[Na+].[Cl-]>C1COCC1>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[C:16]([CH:17]([CH3:19])[CH3:18])=[C:15]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:14][C:12]1=[O:13])[CH2:8]2

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 57495623Adamantan-2-yl-3-(1-benzyl-3-methyl-2-oxo-butyl)-urea

생성물 1

HCID 249655011-Adamantan-2-yl-4-benzyl-5-isopropyl-1,3-dihydro-imidazol-2-one수율 18.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Adamantan-2-yl-3-(1-benzyl-3-methyl-2-oxo-butyl)-urea (100 mg) was dissolved in dry THF (2 mL) and treated with 25% HCl (5 mL) at 60° C. for 3.5 hours. The mixture was cooled, poured into ice cold 3M NaOH, saturated with NaCl. The mixture was extracted with ethyl acetate and the organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography using a gradient of 10 to 40% ethyl acetate in heptane as an eluent. Fractions containing the desired material were combined and evaporated to give 1-adamantan-2-yl-4-benzyl-5-isopropyl-1,3-dihydro-imidazol-2-one as a white foam (18 mg). MS (EI): 350.3 (M+).

후처리

  1. temperatureThe mixture was cooled
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. additionFractions containing the desired material
  9. customevaporated

출처 및 근거

ORD 기록
ord-4ba927c375f644f4b85804ddc2f7d578
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129423B2

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