HCID 21468965, compound → HCID 54146231, compound

HRID 866250Notes

Reaction equation

HRID 866250 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 DH 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-e40cf1fce6f94951b488b548edf6afe2
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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