Hydrochloric Acid → pivaloyloxymethyl 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylate

HRID 963682Notes

Reaction equation

HRID 963682 reaction equation
[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:7]2[C:46]([C:50]([O:52][CH2:53][O:54][C:55](=[O:60])[C:56]([CH3:59])([CH3:58])[CH3:57])=[O:51])=[CH:47][CH:48]=[CH:49][C:6]=2[N:5]=1)[CH3:2].Cl>CO>[CH2:1]([O:3][C:4]1[N:8]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[NH:26][N:25]=[N:24][N:23]=3)=[CH:14][CH:15]=2)[C:7]2[C:46]([C:50]([O:52][CH2:53][O:54][C:55](=[O:60])[C:56]([CH3:59])([CH3:58])[CH3:57])=[O:51])=[CH:47][CH:48]=[CH:49][C:6]=2[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19083195pivaloyloxymethyl 2-ethoxy-1-[2'-(N-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylate

Product 1

HCID 178467381pivaloyloxymethyl 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylateYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 2.0 g of pivaloyloxymethyl 2-ethoxy-1-[2'-(N-triphenylmethyl-1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylate were added 30 mL of methanol and 6 mL of 1N-hydrochloric acid and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was then concentrated under reduced pressure and extracted using ethyl acetate and water. The organic layer was separated and concentrated under reduced pressure to give an oil. This oil was purified by silica gel chromatography (100 mL, methylene chloride-methanol=10:1) to provide 1.13 g of pivaloyloxymethyl 2-ethoxy-1-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methylbenzimidazole-7-carboxylate (yield 80%).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. extractionextracted
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. customto give an oil
  6. customThis oil was purified by silica gel chromatography (100 mL, methylene chloride-methanol=10:1)

Sources & evidence

ORD record
ord-593d50ca063148619b48758098ba350f
Source dataset
uspto-grants-1998_06
Patent number
US05763619

Reaction notes

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