Triphenylphosphine → HCID 23582845, compound

HRID 2239311Notes

Reaction equation

HRID 2239311 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]([C:5]1[CH:6]=[C:7]([OH:22])[C:8]2[N:12]=[C:11]([CH3:13])[N:10](C(OC(C)(C)C)=O)[C:9]=2[CH:21]=1)=[O:4].[F:24][C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27](O)[CH2:28][CH2:29][O:30]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[OH-].[Na+]>C1(C)C=CC=CC=1.CO>[F:24][C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH:27]([O:22][C:7]1[C:8]3[N:12]=[C:11]([CH3:13])[NH:10][C:9]=3[CH:21]=[C:5]([C:3]([N:2]([CH3:1])[CH3:23])=[O:4])[CH:6]=1)[CH2:28][CH2:29][O:30]2

Participants

8

Reactant 5

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68574541HCID 68574541, compoundHCID 68574581HCID 68574581, compound

Product 1

HCID 23582845HCID 23582845, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a stirred mixture of 1,1-dimethylethl 6-[(dimethylamino)carbonyl]-4-hydroxy-2-methyl-1H-benzimidazole-1-carboxylate (1.00 g, 3.13 mmol, STEP 2), 5-fluoro-3,4-dihydro-2H-chromen-4-ol (948 mg, 5.64 mmol, STEP 3-1) and triphenylphosphine (2.57 g, 9.79 mmol) in toluene (50 mL) was added diisopropyl azodicarboxylate (DIAD) (1.98 g, 4.90 mmol) at room temperature. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuum. The residue was dissolved in tetrahydrofuran (30 mL) and methanol (15 mL), and sodium hydroxide (750 mg, 18.8 mmol) was added to the mixture at room temperature. After stirring at room temperature for 1 hour, the mixture was quenched with saturated sodium dihydrogenphosphate aqueous solution, and extracted with ethyl acetate. The organic layers were combined, dried over magnesium sulfate and concentrated in vacuum. The residue was purified by column chromatography on silica gel (dichloromethane only then ethyl acetate methanol 10:1 as an eluent) to afford the title compound as a white solid (510 mg, 50%).

Workup

  1. concentrationconcentrated in vacuum
  2. dissolutionThe residue was dissolved in tetrahydrofuran (30 mL)
  3. stirringAfter stirring at room temperature for 1 hour
  4. customthe mixture was quenched with saturated sodium dihydrogenphosphate aqueous solution
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuum
  8. customThe residue was purified by column chromatography on silica gel (dichloromethane only

Sources & evidence

ORD record
ord-d99b894e8bfc4d8797830bd160400e70
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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