Ethanol → HCID 53633683, compound

HRID 1734634Notes

Reaction equation

HRID 1734634 reaction equation
C([O:4][CH:5]1[CH2:9][CH:8]([CH2:10][O:11]C(=O)C)[CH2:7][CH:6]1[N:15]1[C:19]2[CH:20]=[C:21]([Cl:25])[C:22]([Cl:24])=[CH:23][C:18]=2[N:17]=[C:16]1[Br:26])(=O)C.C(=O)([O-])[O-].[Na+].[Na+].C(O)C.CO>O.C(O)(=O)C>[Br:26][C:16]1[N:15]([CH:6]2[CH2:7][CH:8]([CH2:10][OH:11])[CH2:9][CH:5]2[OH:4])[C:19]2[CH:20]=[C:21]([Cl:25])[C:22]([Cl:24])=[CH:23][C:18]=2[N:17]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 10340Sodium CarbonateHCID 67613748HCID 67613748, compound

Product 1

HCID 53633683HCID 53633683, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

(±)-(1R*, 2R*,4S*)-4-(Acetoxymethyl)-2-(2-bromo-5,6-dichloro-1H-benzimidazol-1-yl)-cyclopentyl acetate (2.75 g, 5.92 mmol) was added to a stirred mixture of sodium carbonate (0.63 g) in water (11 mL)-ethanol (55 mL)-methanol (55 mL). After 2 hours at ambient temperature, the pH was adjusted to 7 with glacial acetic acid. Volatiles were removed in vacuo and the residue triturated with water (30 mL) and filtered to give white solid. Recrystallization of the solid from 1:1 ethanol-methanol gave title compound as white powder (1.62 g, 72%), m.p. 218°-220° C.; 1H-NMR (DMSO-d6)δ: 8.18 (s, 1, benzimidazole H7), 7.97 (s, 1, benzimidazole H4), 5.20 (m, 1, OH), 4.95 (m, 1, OH), 4.80-4.60 (m, 2, OCH and NCH), 3.50-3.40 (m, 2, OCH2), 2.45-2.20 (m, 1, CH), 2.20-1.60 (m, 4, 4CH); mass spectrum (CI): 379 (M+1).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue triturated with water (30 mL)
  3. filtrationfiltered
  4. customto give white solid
  5. customRecrystallization of the solid from 1:1 ethanol-methanol

Sources & evidence

ORD record
ord-0bfe6bf10e964b50b91625daf71a07ed
Source dataset
uspto-grants-1996_07
Patent number
US05534535

Reaction notes

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