Acetic Acid → HCID 131727532, compound

HRID 225970Notes

Reaction equation

HRID 225970 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH2:10][C@@H:11]1[CH2:15][C:14](=[N:16][O:17][CH3:18])[CH2:13][N:12]1[C:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)=[O:20].C(O)(=O)C>ClCCl>[CH3:18][O:17][N:16]=[C:14]1[CH2:15][C@@H:11]([CH2:10][C:9]2[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N:8]=2)[N:12]([C:19]([C:21]2[CH:22]=[CH:23][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:25][CH:26]=2)=[O:20])[CH2:13]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 131727533HCID 131727533, compound

Product 1

HCID 131727532HCID 131727532, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-(2-aminophenyl)-2-[(2S,4EZ)-1-(biphenyl-4-ylcarbonyl)-4-(methoxy imino)pyrrolidin-2-yl]acetamide (Example 11, 21 mg, 0.05 mmol) and acetic acid (0.1 ml) in dichloromethane (1 ml) was stirred overnight. The organic phase was washed with NaHCO3. The organic phase was dried (MgSO4) and concentrated to afford (3EZ,5S)-5-(1H-benzimidazol-2-ylmethyl)-1-(biphenyl-4-ylcarbonyl)pyrrolidin-3-one O-methyloxime (14 mg). Yield: 65%. HPLC purity: 93%

Workup

  1. washThe organic phase was washed with NaHCO3
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ec0f0e1e085542679be31d1ace719330
Source dataset
uspto-grants-2009_07
Patent number
US07557136B2

Reaction notes

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