Potassium Hydroxide → Bicalutamide

HRID 719849

반응식

HRID 719849 반응식
[C:1]([C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8](=[O:21])[C:9]([OH:20])([CH3:19])[CH2:10][S:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[CH:5][C:4]=1[C:24]([F:27])([F:26])[F:25])#[N:2].C1C=C(C(O)=[O:35])C(C(OO)=O)=CC=1.[OH-:41].[K+]>C(OCC)(=O)C>[C:1]([C:3]1[CH:23]=[CH:22][C:6]([NH:7][C:8](=[O:21])[C:9]([OH:20])([CH3:19])[CH2:10][S:11]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)(=[O:35])=[O:41])=[CH:5][C:4]=1[C:24]([F:27])([F:25])[F:26])#[N:2]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 75329Monoperoxyphthalic acidHCID 9800987Bicalutamide sulfide

생성물 1

HCID 2375Bicalutamide수율 91.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

반응 조건

온도
60 °C

실험 절차

4′-Cyano-3-(4-fluorophenylthio)-2-hydroxy-2-methyl-3′-trifluoromethylpropionanilide (12.20 g, 30.6 mmol) and ethyl acetate (20 ml) were successively charged in a 200 ml four-neck flask, and the mixture was stirred under ice-cooling (2° C.–7° C.). A solution of mono-perphthalic acid in ethyl acetate (166.58 g, net 22.31 g, 122.5 mmol) was dropwise added at not higher than 10° C., and the mixture was stirred for 1 hr. A 20% KOH solution (117.5 g) was dropwise added thereto and the mixture was partitioned. The aqueous layer was extracted with ethyl acetate (30 ml). The combined organic layer was washed with a solution of sodium pyrosulfite (3.0 g) dissolved in deionized water (30 ml), dried over magnesium sulfate and concentrated under reduced pressure. Ethyl acetate (66 ml) was added to the residue and the mixture was heated to 60° C. n-Heptane (40 ml) was added dropwise at a temperature of 60° C.–65° C. over 40 min. After the completion of the dropwise addition, the mixture was allowed to cool to room temperature (about 20° C.–25° C.) and filtrated to give 4′-cyano-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methyl-3′-trifluoromethylpropionanilide (12.24 g, yield 91.2%). Purity 99.97%.

후처리

  1. temperaturecooling (2° C.–7° C.)
  2. stirringthe mixture was stirred for 1 hr
  3. customthe mixture was partitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate (30 ml)
  5. washThe combined organic layer was washed with a solution of sodium pyrosulfite (3.0 g)
  6. dissolutiondissolved in deionized water (30 ml)
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. additionEthyl acetate (66 ml) was added to the residue
  10. additionwas added dropwise at a temperature of 60° C.–65° C. over 40 min
  11. additionAfter the completion of the dropwise addition
  12. temperatureto cool to room temperature (about 20° C.–25° C.)
  13. filtrationfiltrated

출처 및 근거

ORD 기록
ord-083c17ce35704e82a628968ade3db0a5
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132560B2

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