Trifluoroacetic acid → 1-benzyl-7-methyl-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

HRID 1106927Notes

Reaction equation

HRID 1106927 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]([CH3:21])[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][C:9]1=[O:29])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]([CH3:21])[CH2:13][CH2:12][NH:11][CH2:10][C:9]1=[O:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 187882171-benzyl-4-tert-butyloxycarbonyl-7-methyl-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

Product 1

HCID 187881341-benzyl-7-methyl-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-benzyl-4-tert-butyloxycarbonyl-7-methyl-2-oxo-2,3,4,5,6,7-hexahydro-1H-1,4-benzodiazonine (160 mg, 0.41 mmol) in chloroform (2 ml) was stirred with trifluoroacetic acid (3 ml) at room temperature for 30 minutes. The mixture was evaporated to dryness and the residue partitioned between chloroform and saturated potassium carbonate solution (30 ml/1:2). The organic layer was separated and dried (MgSO4). Filtration and evaporation of the solvent gave the product. (98 mg, 81%).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue partitioned between chloroform and saturated potassium carbonate solution (30 ml/1:2)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and evaporation of the solvent
  6. customgave the product

Sources & evidence

ORD record
ord-b45f9f07659b4274b313bbf4d127dc06
Source dataset
uspto-grants-2000_05
Patent number
US06057311

Reaction notes

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