Ethanol → HCID 15280847, compound

HRID 1609043Notes

Reaction equation

HRID 1609043 reaction equation
C([O:4][C@H:5]1[C@H:9]([N:10]2[C:14]3[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH2:8][C@H:7]([CH2:21][O:22]C(=O)C)[C@H:6]1[O:26]C(=O)C)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].C(O)C.CO>O.C(O)(=O)C>[Cl:19][C:17]1[C:16]([Cl:20])=[CH:15][C:14]2[N:10]([C@H:9]3[C@H:5]([OH:4])[C@H:6]([OH:26])[C@@H:7]([CH2:21][OH:22])[CH2:8]3)[CH:11]=[N:12][C:13]=2[CH:18]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 10340Sodium CarbonateHCID 15280845HCID 15280845, compound

Product 1

HCID 15280847HCID 15280847, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

(1S,2R,3R,5R)-3-(Acetoxymethyl)-5-(5,6-dichloro-1H-benzimidazol-1-yl)-1,2-cyclopentanediyl diacetate (0.96 g, 2.17 mmol) and sodium carbonate (0.230 g, 2.17 mmol) were stirred in water (3 mL)-ethanol(15 mL)-methanol(15 mL) at ambient temperature for 24 hours. The pH was adjusted to 7 with acetic acid and the volatiles removed in vacuo. The residual solid was slurried in water (25 mL) and filtered. Resolidification from 2:1 ethanol-methanol gave (1 S,2R,3R,5R)-5-(5,6-dichloro-1H-benzimidazol-1-yl)-3-(hydroxymethyl)-1,2-cyclopentanediol as white powder (408 mg, 60%), m.p. 222°-225° C.; 1H-NMR(DMSO-d6) δ: 8.49, 8.09, and 7.96 (all s, 1 each, 3 benzimidazole CH), 5.04 (d, J=7.0 Hz, 1, OH), 4.87 (t, J=5.1 Hz, 1, CH2OH), 4.84.6 (m overlapping d at 4.76, J=4.3 Hz, 2, NCH and OH), 4.25-4.10 (m, 1, OCH), 3.9-3.8 (m, 1, OCH), 3.6-3.45 (m, 2, CH2O), 2.45-2.25 (m, 1, CH), 2.2-2.0 (m, 1, CH), 1.85-1.65 (m, 1, CH); mass spectrum(CI): 317 (M+1); [α]20578 -12.9°, [α]20546 -14.1° (c=0.255, methanol).

Workup

  1. customthe volatiles removed in vacuo
  2. filtrationfiltered

Sources & evidence

ORD record
ord-7281c46d4d74447ba5b2e4f2ea7c4b2d
Source dataset
uspto-grants-1995_03
Patent number
US05399580

Reaction notes

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