Water → HCID 69969505, compound

HRID 1937743Notes

Reaction equation

HRID 1937743 reaction equation
[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:25])[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[C:8]=2[CH:26]=1)(=[O:3])[CH3:2].O.FC(F)(F)C(O)=[O:31].FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=O>C(#N)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:17]([NH:16][C@H:9]2[C:8]3[CH:26]=[C:4]([C:1](=[O:3])[CH2:2][OH:31])[CH:5]=[CH:6][C:7]=3[O:12][C:11]([CH3:14])([CH3:13])[C@@H:10]2[OH:15])=[O:25])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 193943Carabersat

Product 1

HCID 69969505HCID 69969505, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3R,4S)-6-Acetyl-4-(4-fluorobenzamido)-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran D5 (1.83 g, 5.0 mmol) (Example 20 of WO92/22293) was dissolved in acetonitrile (25 ml), 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 foam was purified by column chromatography on silica, eluting with 20% to 50% ethyl acetate in hexane to afford the title compound as a white solid (0.44 g, 24%), m.p. 216° C.

Workup

  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 foam was purified by column chromatography on silica
  10. washeluting with 20% to 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-327578b0d2f648d58c7dfcc8427d5874
Source dataset
uspto-grants-2002_05
Patent number
US06395909B1

Reaction notes

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