HCID 21468965, compound → HCID 54146231, compound

HRID 1938600Notes

Reaction equation

HRID 1938600 reaction equation
[O:1]=[C:2]([N:30]1[CH2:34][CH2:33][CH2:32][CH:31]1[C:35]([O:37]CC1C=CC=CC=1)=[O:36])[CH:3]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[N:26]=[N:27][NH:28][N:29]=3)=[CH:18][C:13]=2[N:12]=[CH:11]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]>CO>[O:1]=[C:2]([N:30]1[CH2:34][CH2:33][CH2:32][C@H:31]1[C:35]([OH:37])=[O:36])[CH:3]([N:10]1[C:14]2[CH:15]=[CH:16][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25]3[N:26]=[N:27][NH:28][N:29]=3)=[CH:18][C:13]=2[N:12]=[CH:11]1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH3:9]

Participants

3

Reactant 1

HCID 21468965HCID 21468965, compound

Product 1

HCID 54146231HCID 54146231, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl 1-[1-oxo-2-[5-[2-(2H-tetrazol-5-yl)phenyl]-1H-benzimidazole-1-yl]octyl]-2-pyrrolidinecarboxylate (0.388 mmoles, 230 mg) was dissolved in 5.0 ml methanol/3.0 ml 2N NaOH and stirred at room temperature for 16 hours. The ethanol was removed in vacuo. The aqueous layer washed with ether. The pH was adjusted to 3.5 using 2N HCl with cooling. The precipitate was filtered and dried to yield 75 mg of 1-[1-Oxo-2-[5-[2-(2H-tetrazol-5-yl)phenyl]-1H-benzimidazole-1-yl]octyl]-L-proline. (MS)

Workup

  1. customThe ethanol was removed in vacuo
  2. washThe aqueous layer washed with ether
  3. temperaturewith cooling
  4. filtrationThe precipitate was filtered
  5. customdried

Sources & evidence

ORD record
ord-4d46e7f46e1d4f88b8ce04760798b364
Source dataset
uspto-grants-1997_12
Patent number
US05693633

Reaction notes

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