Acetic Anhydride → HCID 68415475, compound

HRID 220282Notes

Reaction equation

HRID 220282 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:9][CH2:10][CH2:11][C:12]1[NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([NH2:21])[C:14]=2[N:13]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:1]([O:5][C:6](=[O:22])[N:7]([CH2:9][CH2:10][CH2:11][C:12]1[NH:16][C:15]2[CH:17]=[CH:18][CH:19]=[C:20]([NH:21][C:23](=[O:25])[CH3:24])[C:14]=2[N:13]=1)[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 68414384HCID 68414384, compound

Product 1

HCID 68415475HCID 68415475, compound

Procedure

A solution of 3.66 g of [3-(4-amino-1H-benzoimidazol-2-yl)-propyl]-methyl-carbamic acid tert-butyl ester in 40 mL of acetic anhydride was refluxed for 2 h. The excess of acetic anhydride was evaporated off and the residue was treated with 16 mL of EtOH and IM-NaOH until pH 10 then extracted with EtOAc. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. Purification by CC using EtOAc/MeOH 100/1 to 90/1 yielded 1.86 g of [3-(4-acetylamino-1H-benzoimidazol-2-yl)-propyl]-methyl-carbamic acid tert-butyl ester as yellow foam.

Workup

  1. customThe excess of acetic anhydride was evaporated off
  2. additionthe residue was treated with 16 mL of EtOH and IM-NaOH until pH 10
  3. extractionthen extracted with EtOAc
  4. dry with materialThe organic phase was dried over anh. Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by CC

Sources & evidence

ORD record
ord-0ae2e56943aa4ad9929c67571ab01696
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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