Indomethacin → Acemetacin

HRID 746267

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HRID 746267 반응식
[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([OH:25])=[O:24].[F-].[K+].[C:28]([O-:32])(=[O:31])[CH2:29]C.[Na+].ClCC(OC(C)(C)C)=O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[CH3:1][C:2]1[N:10]([C:11]([C:13]2[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=2)=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([O:20][CH3:21])=[CH:5][C:4]=2[C:3]=1[CH2:22][C:23]([O:25][CH2:29][C:28]([OH:32])=[O:31])=[O:24]

참가 물질

8

반응물 5

HCID 3715IndomethacinHCID 10340Sodium CarbonateHCID 66052tert-Butyl chloroacetateHCID 522689Potassium FluorideHCID 2723816Sodium Propionate

생성물 1

HCID 1981Acemetacin수율 95.6%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

One hundred grams of indomethacin, 91.25 g of potassium fluoride and 13.5 g of sodium propionate were suspended in 500 ml of dimethylformamide, followed by an addition of 64.31 g of t-butyl chloroacetate. The resultant mixture was stirred and then stirred for 1 hour in a water bath of 90° C. After cooling, the mixture was poured into 5 liters of a 10% solution of sodium carbonate in water, followed by an addition of water to make the total volume be 20 liters. The resulting yellowish solid deposit was separated and then taken up in 1.65 liters of benzene. The thus-prepared solution was washed with water and, after drying, the solvent was driven off. The residue was recrystallized from n-hexane, thereby obtaining 126.1 g of the t-butyl ester of acemetacin as pale yellowish crystals (yield: 95.6%)

후처리

  1. temperatureAfter cooling
  2. customThe resulting yellowish solid deposit was separated
  3. washThe thus-prepared solution was washed with water
  4. customafter drying
  5. customThe residue was recrystallized from n-hexane

출처 및 근거

ORD 기록
ord-d173bdb614f940b298969b5d4418ca58
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04603210

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