Water → HCID 57193939, compound

HRID 1937742Notes

Reaction equation

HRID 1937742 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:26])[C:18]3[CH:23]=[CH:22][C:21]([F:24])=[C:20]([Cl: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>[Cl:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[F:24])[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]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 6918324Tonabersat

Product 1

HCID 57193939HCID 57193939, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(3S,4S)-6-Acetyl-4-(3-chloro-4-fluorobenzamido)-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran D4 (1.97 g, 5.0 mmol) (Example 17 of WO95/34545) 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 giving a yellow solid which was isolated by filtration and recrystallised from ethyl acetate/hexane to give the title compound as a white solid (0.48 g, 24%), m.p. 200° C.

Workup

  1. temperatureunder reflux for three hours
  2. temperatureto cool
  3. customthe acetonitrile was removed in vacuo
  4. customgiving a yellow solid which
  5. customwas isolated by filtration
  6. customrecrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d92f1003b9f34c8e8efb2b9e1411060d
Source dataset
uspto-grants-2002_05
Patent number
US06395909B1

Reaction notes

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