Ethanol → HCID 54016514, compound

HRID 1734650Notes

Reaction equation

HRID 1734650 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].CO.C(O)C.C([O:15][CH:16]1[CH:20]([N:21]2[C:25]3[CH:26]=[C:27]([Cl:31])[C:28]([Cl:30])=[CH:29][C:24]=3[N:23]=[C:22]2[I:32])[CH2:19][CH:18]([CH2:33][O:34]C(=O)C)[CH:17]1[O:38]C(=O)C)(=O)C>O.C(O)(=O)C>[Cl:30][C:28]1[C:27]([Cl:31])=[CH:26][C:25]2[N:21]([CH:20]3[CH:16]([OH:15])[CH:17]([OH:38])[CH:18]([CH2:33][OH:34])[CH2:19]3)[C:22]([I:32])=[N:23][C:24]=2[CH:29]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 10340Sodium CarbonateHCID 54219555HCID 54219555, compound

Product 1

HCID 54016514HCID 54016514, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium carbonate (40 mg, 0.37 mmol) was dissolved in water (0.7 mL) and methanol (3 mL) and ethanol (3 mL) were added. To this stirred mixture was added (±)(1R*, 2S*, 3S*, 5S*)-3-(acetoxymethyl)-5-(5,6-dichloro-2-iodo-1H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (215 mg, 0.37 mmol). After 2 hours at ambient temperature, acetic acid was added to adjust the pH to 7 and volatiles were evaporated in vacuo. Resolidification of the residual solid from 3:1 ethanol-water gave (±)-(1R*, 2S*, 3S*, 5S*)-5-(5,6-dichloro-2-iodo-1H-benzimidazol-1-yl)-3-(hydroxymethyl)-1,2-cyclopentanediol as a white powder (153 mg, 94%), m.p. 209°-210° C. dec.; 1H-NMR(DMSO-d6)δ: 8.22 and 7.91 (both s, 2, 2 aromatic CH), 5.12 (t, J=4.5 Hz, 1, OH), 4.95 (d, J=6.2 Hz, 1, OH), 4.9-4.8 (m, 1, NCH), 4.70 (t, J=3.5 Hz, 1, OH), 4.6-4.5 (m, 1, OCH), 3.9-3.8 (m, 1, OCH), 3.7-3.6 and 3.55-3.45 (both m, 1 each, OCH2), 2.2-2.0 (m, 3, CH2 and CH); mass spectrum(CI): 443 (M+1).

Workup

  1. customwere evaporated in vacuo

Sources & evidence

ORD record
ord-e32abe6382994cc5bfeeb62a1e4e63b2
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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