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

HRID 466814

反応式

HRID 466814 の反応式
[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

参加物

4

反応物 3

HCID 11430Potassium Carbonate2 回HCID 13385Vinylene carbonateHCID 198147681-Azabicyclo[3.1.1]heptane-5-carboxamide

生成物 1

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

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f7306b3e19a547bb8a3bbe1912694ec3
出典データセット
uspto-grants-1992_10
特許番号
US05157160

関連ノート

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