Acetic Anhydride → (S)-1-[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid acetyl-amide

HRID 2374792Notes

Reaction equation

HRID 2374792 reaction equation
[C:1]([C:3]1[CH:38]=[CH:37][C:6]([CH2:7][C@@:8]2([CH3:36])[N:12]3[C:13]([S:16]([N:19]4[CH2:23][CH2:22][CH2:21][C@H:20]4[C:24]([NH2:26])=[O:25])(=[O:18])=[O:17])=[CH:14][N:15]=[C:11]3[N:10]([C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=3)[C:9]2=[O:35])=[CH:5][CH:4]=1)#[N:2].[C:39](OC(=O)C)(=[O:41])[CH3:40]>>[C:39]([NH:26][C:24]([C@@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[S:16]([C:13]1[N:12]2[C@@:8]([CH2:7][C:6]3[CH:37]=[CH:38][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)([CH3:36])[C:9](=[O:35])[N:10]([C:27]3[CH:28]=[C:29]([Cl:34])[CH:30]=[C:31]([Cl:33])[CH:32]=3)[C:11]2=[N:15][CH:14]=1)(=[O:18])=[O:17])=[O:25])(=[O:41])[CH3:40]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 12136443(S)-1-[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid amide

Product 1

HCID 12136444(S)-1-[(R)-5-(4-cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid acetyl-amide

Conditions

Temperature
100 °C

Procedure

(S)-1-[(R)-5-(4-Cyano-benzyl)-7-(3,5-dichloro-phenyl)-5-methyl-6-oxo-6,7-dihydro-5H-imidazo[1,2-a]imidazole-3-sulfonyl]-pyrrolidine-2-carboxylic acid amide (98 mg, 0.17 mmol) was dissolved in acetic anhydride (3 mL, 0.05 M). The reaction was heated to 100° C. for 18 h. The mixture was concentrated, toluene added, and the mixture concentrated again. The residue was chromatographed over silica with a solvent system of 10% MeOH in methylene chloride to provide 19 mg of the title compound as a white solid (M+1, 615).

Workup

  1. concentrationThe mixture was concentrated
  2. additiontoluene added
  3. concentrationthe mixture concentrated again
  4. customThe residue was chromatographed over silica with a solvent system of 10% MeOH in methylene chloride

Sources & evidence

ORD record
ord-8ea8b4980860476f9e3346f2d124e878
Source dataset
uspto-grants-2008_12
Patent number
US07462637B2

Reaction notes

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