Acetic Anhydride → HCID 178418641, compound

HRID 1418619Notes

Reaction equation

HRID 1418619 reaction equation
[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[C:23](=[NH:26])[NH:24][OH:25])=[CH:13][CH:12]=2)[C:8]2[C:27]([C:31]([O:33][CH3:34])=[O:32])=[CH:28][CH:29]=[CH:30][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].C(N(CC)CC)C.[C:42](OC(=O)C)(=[O:44])[CH3:43]>ClCCl>[C:42]([O:25][NH:24][C:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:9]2[C:8]3[C:27]([C:31]([O:33][CH3:34])=[O:32])=[CH:28][CH:29]=[CH:30][C:7]=3[N:6]=[C:5]2[CH2:1][CH2:2][CH2:3][CH3:4])=[CH:12][CH:13]=1)=[NH:26])(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178441474HCID 178441474, compound

Product 1

HCID 178418641HCID 178418641, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-butyl-1-[[2'-(hydroxycarbamimidoyl)biphenyl-4-yl]methyl]bezimidazole-7-carboxylate (1.83 g) in dichloromethane (20 ml) was added triethylamine (0.46 g) and acetic anhydride (0.46 g), and the reaction mixture was stirred at room temperature for 2 hours. After evaporation of the solvent, the residue was partitioned between ethylacetate and water and the organic layer was washed with an aqueous solution of NaHCO3 and water. The solution was dried and concentrated to dryness to give a pale yellow solid (1.99 g, quant.)

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was partitioned between ethylacetate and water
  3. washthe organic layer was washed with an aqueous solution of NaHCO3 and water
  4. customThe solution was dried
  5. concentrationconcentrated to dryness
  6. customto give a pale yellow solid (1.99 g, quant.)

Sources & evidence

ORD record
ord-676f2b00cb4a4589963dbc091bd2844b
Source dataset
uspto-grants-1999_03
Patent number
US05883111

Reaction notes

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