HCID 18957796, compound → HCID 18957776, compound

HRID 2379318Notes

Reaction equation

HRID 2379318 reaction equation
[CH:1]1([C:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]([CH2:17][CH3:18])[C:9](=[O:19])[CH:8]([NH:20]C(OCC3C=CC=CC=3)=O)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)=O.CO.[Pd]>[NH2:20][CH:8]1[N:7]=[C:6]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][CH3:18])[C:9]1=[O:19]

Participants

4

Reactant 1

HCID 18957796HCID 18957796, compound

Product 1

HCID 18957776HCID 18957776, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent2×

Procedure

5-Cyclopentyl-1,3-dihydro-1-ethyl-3(R,S)[(benzyloxycarbonyl)amino]-2H-1,4-benzodiazepin-2-one (0.5 g, 1.23 mmol) was dissolved in formic acid/methanol (50 ml of a 4.5% (v/v) solution), and added, over 5 min, to a stirred suspension of 10% palladium on carbon (200 mg, 40% (w/w)) in formic acid/methanol (10 ml). After 10 min the catalyst was removed by filtration, washed with methanol and acetone and the flitrate concentrated. The residue was partitioned between ethyl acetate (100 ml) and 10% sodium carbonate solution (100 ml). The organic phase was separated, dried (Na2SO4) and evaporated to give a clear oil which was used without further purification.

Workup

  1. customAfter 10 min the catalyst was removed by filtration
  2. washwashed with methanol and acetone
  3. concentrationthe flitrate concentrated
  4. customThe residue was partitioned between ethyl acetate (100 ml) and 10% sodium carbonate solution (100 ml)
  5. customThe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give a clear oil which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-2de9f191411d41bfa59fe3cc053d13ea
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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