Hydrazine hydrate (1:1) → HCID 54474810, compound

HRID 1734658Notes

Reaction equation

HRID 1734658 reaction equation
C([O:4][CH:5]1[CH:9]([N:10]2[C:14]3[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:13]=3[N:12]=[C:11]2Br)[CH2:8][CH:7]([CH2:22][O:23]C(=O)C)[CH:6]1[O:27]C(=O)C)(=O)C.O.[NH2:32]N>C(O)C>[Cl:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]2[N:10]([CH:9]3[CH:5]([OH:4])[CH:6]([OH:27])[CH:7]([CH2:22][OH:23])[CH2:8]3)[C:11]([NH2:32])=[N:12][C:13]=2[CH:18]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54404171HCID 54404171, compound

Product 1

HCID 54474810HCID 54474810, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)(1R*, 2S*, 3S*, 5S*)-3-(Acetoxymethyl)-5-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (750 mg, 1.44 mmol) was dissolved in ethanol (10 mL). Hydrazine hydrate (55%, 0.41 mL, 7.2 mmol) was added and the solution was refluxed for 2 hours. Volatiles were evaporated and the residual white solid was resolidified from ethanol-water and stirred with Raney nickel (preequilibrated under hydrogen) in methoxyethanol (20 mL) for 30 minutes. Catalyst was filtered off and the filtrate made slightly basic with aqueous sodium hydroxide to complete removal of the acetate groups. The solution was neutralized, and volatiles evaporated. The residual solid was recrystallized from ethanol-water to give title compound as pale pink solid (97 mg, 20%), m.p. 283°-284° C. dec.; 1H-NMR(DMSO-d6)δ: 7.61 and 7.30 (both s, 2, aromatic CH), 6.65 (br s, 2, NH2), 5.07 (t, J=4.3 Hz, 1, OH), 4.80 (d, J=7.0 Hz, 1, OH), 4.66 (d, J=3.7 Hz, 1, OH), 4.65-4.50 (m, 1, NCH), 4.45-4.30 (m, 1, OCH), 3.90-4.80 (m, 1, OCH), 3.70-3.40 (two m, 2, OCH2), 2.20-1.80 (m, 3, CH2 and CH of cyclopentane); mass spectrum (CI): 332 (M+1).

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. customVolatiles were evaporated
  3. filtrationCatalyst was filtered off
  4. customremoval of the acetate groups
  5. customvolatiles evaporated
  6. customThe residual solid was recrystallized from ethanol-water

Sources & evidence

ORD record
ord-0b94678a6b9b4b0ba1769482815e199a
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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