Potassium Carbonate → 5-(1,3-Oxazol-2-yl)-1-azabicyclo[3.1.1]heptane oxalate salt

HRID 466814

반응식

HRID 466814 반응식
[N:1]12[CH2:7][C:5]([C:8]([NH2:10])=[O:9])([CH2:6]1)[CH2:4][CH2:3][CH2:2]2.[C:11]1(=O)[O:15][CH:14]=[CH:13][O:12]1.[C:17](=[O:20])([O-:19])[O-].[K+].[K+]>>[C:11]([OH:15])(=[O:12])[C:17]([OH:19])=[O:20].[O:9]1[CH:14]=[CH:13][N:10]=[C:8]1[C:5]12[CH2:7][N:1]([CH2:6]1)[CH2:2][CH2:3][CH2:4]2

참가 물질

4

반응물 3

HCID 11430Potassium Carbonate2회HCID 13385Vinylene carbonateHCID 198147681-Azabicyclo[3.1.1]heptane-5-carboxamide

생성물 1

HCID 198147655-(1,3-Oxazol-2-yl)-1-azabicyclo[3.1.1]heptane oxalate salt

반응 조건

온도
120 °C

실험 절차

A well stirred mixture of 1-azabicyclo[3.1.1]hept-5-ylcarboxamide (D12, 640 mg, 0.0046 mole) and vinylene carbonate (600 mg, 0.0069 mole) in polyphosphoric acid (25 g) was heated at 120° C. for 1 h. The hot solution was then poured cautiously, with good stirring, into excess potassium carbonate solution. The aqueous mixture was saturated with potassium carbonate and extracted with ethyl acetate (1×100 ml), followed by chloroform (1×100 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo at room temperature. The residue was immediately chromatographed on basic alumina eluting initially with ethyl acetate, increasing to 15% methanol/ethyl acetate to give a colourless oil (60 mg). This was converted to its oxalate salt and recrystallised from methanol/ether to give the title compound (E4) as a white solid (65 mg, 6%) m.p. 165°-166° C.

후처리

  1. extractionextracted with ethyl acetate (1×100 ml)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo at room temperature
  4. customThe residue was immediately chromatographed on basic alumina eluting initially with ethyl acetate
  5. temperatureincreasing to 15% methanol/ethyl acetate

출처 및 근거

ORD 기록
ord-f7306b3e19a547bb8a3bbe1912694ec3
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05157160

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