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Water → HCID 9886735, 화합물

HRID 1937741
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HRID 1937741 반응식
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C:11]([CH3:14])([CH3:13])[C@H:10]([OH:15])[C@@H:9]([NH:16][C:17](=[O:26])[C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[C:20]([F:25])[CH:19]=3)[C:8]=2[CH:27]=1)(=[O:3])[CH3:2].O.FC(F)(F)C(O)=[O:32].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O>C(#N)C>[F:24][C:22]1[CH:23]=[C:18]([CH:19]=[C:20]([F:25])[CH:21]=1)[C:17]([NH:16][C@H:9]1[C:8]2[CH:27]=[C:4]([C:1](=[O:3])[CH2:2][OH:32])[CH:5]=[CH:6][C:7]=2[O:12][C:11]([CH3:14])([CH3:13])[C@@H:10]1[OH:15])=[O:26]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 170378Tidembersat

생성물 1

HCID 9886735HCID 9886735, 화합물수율 36%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

(3R,4S)-6-Acetyl-4-(3,5-difluorobenzamido)-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran D3 (1.88 g, 5.0 mmol) (Example 4 of WO95/34545) was dissolved in acetonitrile (25ml), water (5 ml) and trifluoroacetic acid (0.77 ml, 10.0 mmol). [Bis(trifluoroacetoxy)iodo]benzene (4.30 g, 10.0 mmol) was added and the reaction stirred under reflux for three hours. The reaction mixture was allowed to cool and the acetonitrile was removed in vacuo, the resulting material being partitioned between water (50 ml) and dichloromethane (125 ml). The aqueous layer was extracted with further portions of dichloromethane (3×25 ml) and the combined organic extracts were dried over magnesium sulphate, filtered and the solvent removed in vacuo. The resulting yellow solid was purified by column chromatography on silica, eluting with 20% to 40% ethyl acetate in hexane to afford the title compound as a white solid (0.70 g, 36%, m.p. 179.4° C.).

후처리

  1. temperatureunder reflux for three hours
  2. temperatureto cool
  3. customthe acetonitrile was removed in vacuo
  4. customthe resulting material being partitioned between water (50 ml) and dichloromethane (125 ml)
  5. extractionThe aqueous layer was extracted with further portions of dichloromethane (3×25 ml)
  6. dry with materialthe combined organic extracts were dried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customThe resulting yellow solid was purified by column chromatography on silica
  10. washeluting with 20% to 40% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-735a55d5d83d4290a4e1b986af91af95
출처 데이터셋
uspto-grants-2002_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06395909B1

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