p-Toluenesulfonic acid → HCID 57225501、化合物

HRID 1067110ノート

反応式

HRID 1067110 の反応式
O[C@:2]1([C:9]2[O:10][C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=C(C3C=CC=CC=3)[N:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[OH:8].COC(OC)(OC)C.[C:34]1([CH3:44])[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>C(Cl)Cl>[C:34]1([C:44]2[N:13]=[C:9]([C@:2]34[O:8][C@H:3]3[CH2:4][CH2:5][CH2:6][CH2:7]4)[O:10][C:11]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 15050Trimethyl orthoacetateHCID 57102465(1R,2S)-1,2-dihydroxy-1-(4,5-diphenyloxazol-2-yl)cyclohexane

生成物 1

HCID 57225501HCID 57225501、化合物収率 38,251.199%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (1R,2S)-1,2-dihydroxy-1-(4,5-diphenyl-oxazol-2-yl)cyclohexane (18 g) in CH2Cl2 (200 ml) were added orthoacetic acid trimethyl ester (9.7 ml) and p-toluenesulfonic acid (20 mg) at room temperature under N2. After being stirred for 30 minutes, the solvent was evaporated in vacuo. The residue was diluted with CH2Cl2 (200 ml) and acetylbromide (5.8 ml) was added to the solution at 0° C. under N2. After being stirred for 2 hours at room temperature, the solvent was evaporated in vacuo, the residue was diluted with MeOH (200 ml), and K2CO3 (12 g) was added to the solution at room temperature. The mixture was stirred for 2 hours at the same temperature and partitioned between ethyl acetate and water. The organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine. The dried solvent was evaporated in vacuo and the residue was purified by chromatography on silica gel to give (1R,2S)-1-(4,5-diphenyl-oxazol-2-yl)-1,2-epoxycyclohexane (14.1 g).

後処理

  1. customthe solvent was evaporated in vacuo
  2. additionThe residue was diluted with CH2Cl2 (200 ml) and acetylbromide (5.8 ml)
  3. additionwas added to the solution at 0° C. under N2
  4. stirringAfter being stirred for 2 hours at room temperature
  5. customthe solvent was evaporated in vacuo
  6. additionthe residue was diluted with MeOH (200 ml), and K2CO3 (12 g)
  7. additionwas added to the solution at room temperature
  8. stirringThe mixture was stirred for 2 hours at the same temperature
  9. custompartitioned between ethyl acetate and water
  10. washThe organic layer was washed with 1N-HCl, water, sat. NaHCO3 and brine
  11. customThe dried solvent was evaporated in vacuo
  12. customthe residue was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-927f7c0a336c4ce994dc0bd46a5ec461
出典データセット
uspto-grants-2001_06
特許番号
US06245790B1

反応ノート

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