Phenol → HCID 54546801, compound

HRID 1734647Notes

Reaction equation

HRID 1734647 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].C([O:17][CH:18]1[CH:22]([N:23]2[C:27]3[CH:28]=[C:29]([Cl:33])[C:30]([Cl:32])=[CH:31][C:26]=3[N:25]=[C:24]2Br)[CH2:21][CH:20]([CH2:35][O:36]C(=O)C)[CH:19]1[O:40]C(=O)C)(=O)C>CN(C)C=O>[Cl:32][C:30]1[C:29]([Cl:33])=[CH:28][C:27]2[N:23]([CH:22]3[CH:18]([OH:17])[CH:19]([OH:40])[CH:20]([CH2:35][OH:36])[CH2:21]3)[C:24]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[N:25][C:26]=2[CH:31]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 54404171HCID 54404171, compound

Product 1

HCID 54546801HCID 54546801, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Phenol (72 mg, 0.77 mmol) and anhydrous potassium carbonate (106 mg, 0.77 mmol) were stirred in dry N,N-dimethylformamide (5 mL) under nitrogen for 1.0 hour. (±)(1R*, 2S*, 3S*, 5S*)-3-(Acetoxymethyl)-5-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (400 mg, 0.770 mmol) was added and the mixture stirred at 80° C. (oil bath) for 18 hours. Volatiles were removed in vacuo and the residue partitioned between chloroform and water. The chloroform layer was dried (sodium sulfate) and volatiles evaporated. The residual oil was stirred in 4N ammonia in methanol (30 mL) at ambient temperature for 18 hours. Evaporation and chromatography of the residue on silica gel with elution by 2% methanol-chloroform gave (±)-(1R*, 2S*, 3S*, 5S*)-5-(5,6-dichloro-2-phenoxy-1H-benzimidazol-1-yl)-3-(hydroxymethyl)-1,2-cyclopentanediol as white solid foam from ethyl acetate (215 mg, 68%); 1H-NMR(DMSO-d6)δ: 7.98 and 7.71 (both s, 2, aromatic CH), 7.6-7.3 (m, 5, C6H5), 5.07 (d, J=6.4 Hz, 1, OH), 5.0-4.75 (m overlapping t at 4.95, J=3.1 Hz, total 2, NCH and OH), 4.71 (d, J=3.9 Hz, 1, OH), 4.5-4.35 (m, 1, OCH), 3.9-3.8 (m, 1, OCH), 3.7-3.4 (m, 2, OCH2), 2.3-1.9 (m, 3, CH2 and CH); mass spectrum (CI): 409 (M+1).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue partitioned between chloroform and water
  3. dry with materialThe chloroform layer was dried (sodium sulfate)
  4. customvolatiles evaporated
  5. stirringThe residual oil was stirred in 4N ammonia in methanol (30 mL) at ambient temperature for 18 hours
  6. customEvaporation and chromatography of the residue on silica gel
  7. washwith elution by 2% methanol-chloroform

Sources & evidence

ORD record
ord-be39ce68aa434ee692223ee1aacb36dd
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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