Sulfuric Acid → (R)-3-(4-(2,4-difluorophenyl)pent-4-enoyl)-4-phenyl oxazolidin-2-one

HRID 512802

反応式

HRID 512802 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:15])[CH2:10][CH2:11][C:12]([OH:14])=O.C(Cl)(=O)C(C)(C)C.[C:23]1([C@@H:29]2[CH2:33][O:32][C:31](=[O:34])[NH:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.S(=O)(=O)(O)O>ClCCl.CN(C)C1C=CN=CC=1.CN(C)C=O.C(N(CC)CC)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[CH2:15])[CH2:10][CH2:11][C:12]([N:30]1[C@H:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:33][O:32][C:31]1=[O:34])=[O:14]

参加物

9

反応物 4

HCID 1118Sulfuric AcidHCID 62493Pivaloyl chlorideHCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-oneHCID 11117352Posacozole Related Compound 2

生成物 1

HCID 71534790(R)-3-(4-(2,4-difluorophenyl)pent-4-enoyl)-4-phenyl oxazolidin-2-one

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回HCID 8471Triethylamine溶媒

反応条件

温度
12.5 °C

実験手順

To a solution of 4-(2,4-difluorophenyl)pent-4-enoic acid compound of formula-2 (100 g) in dichloromethane (800 ml), added triethylamine (97.4 g) at 25-30° C. and the reaction mixture was stirred for 15 minutes at the same temperature. The reaction mixture was cooled to 10-15° C. and added pivaloyl chloride (63 g) to the reaction mixture over a period of 45 minutes. Temperature of the reaction mixture was raised to 25-30° C. and the reaction mixture was stirred for 2 hours at 25-30° C. After completion of the reaction, added (R)-4-phenyloxazolidin-2-one compound of formula-3 (69 g), 4-dimethylamino pyridine (21 g), dimethyl formamide (37 ml) and followed by dichloromethane (200 ml) to the above reaction mixture. Heated the reaction mixture to 45° C. and stirred for 2 hours at the same temperature. After completion of the reaction, the reaction mixture was cooled to 25-30° C. Sulfuric acid was added to the reaction mixture and stirred for 15 minutes. Both organic and aqueous layers were separated and the organic layer was washed with water. Distilled off the solvent completely from the organic layer under reduced pressure and isopropyl alcohol was added to the obtained residue at 25-30° C. and stirred for 15 minutes at the same temperature. The reaction mixture was cooled to 0-10° C. and then stirred for 1½ hour at the same temperature. Filtered the obtained solid, washed with chilled isopropyl alcohol and then dried to get title compound.

後処理

  1. temperatureTemperature of the reaction mixture was raised to 25-30° C.
  2. stirringthe reaction mixture was stirred for 2 hours at 25-30° C
  3. customAfter completion of the reaction
  4. temperatureHeated the reaction mixture to 45° C.
  5. stirringstirred for 2 hours at the same temperature
  6. customAfter completion of the reaction
  7. temperaturethe reaction mixture was cooled to 25-30° C
  8. stirringstirred for 15 minutes
  9. customBoth organic and aqueous layers were separated
  10. washthe organic layer was washed with water
  11. distillationDistilled off the solvent completely from the organic layer under reduced pressure and isopropyl alcohol
  12. additionwas added to the obtained residue at 25-30° C.
  13. stirringstirred for 15 minutes at the same temperature
  14. temperatureThe reaction mixture was cooled to 0-10° C.
  15. stirringstirred for 1½ hour at the same temperature
  16. filtrationFiltered the obtained solid
  17. washwashed with chilled isopropyl alcohol
  18. customdried

出典と根拠

ORDレコード
ord-4bef86e05c114ad3891b4f357f4e7c2f
出典データセット
uspto-grants-2015_08
特許番号
US09102664B2

関連ノート

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