Ethanol → HCID 56974635, compound

HRID 1609042Notes

Reaction equation

HRID 1609042 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].CO.C(O)C.C([O:15][C@@H:16]1[C@@H: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][C@@H:18]([CH2:33][O:34]C(=O)C)[C@@H: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]([C@@H:20]3[C@@H:16]([OH:15])[C@@H:17]([OH:38])[C@H: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 86748569HCID 86748569, compound

Product 1

HCID 56974635HCID 56974635, 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-81af7c346aee44eaba7c34f0b5cf9123
Source dataset
uspto-grants-1995_03
Patent number
US05399580

Reaction notes

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