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

HRID 1901979Notes

Reaction equation

HRID 1901979 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-28b3e01ae4e14359a0c930ecd5b4ac96
Source dataset
uspto-grants-1996_11
Patent number
US05578733

Reaction notes

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