Formate → HCID 53887049, compound

HRID 1596337Notes

Reaction equation

HRID 1596337 reaction equation
[CH:1]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:10]([CH2:12][N:13]1[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[C:17]([CH:24]([CH3:26])[CH3:25])=[N:16][CH:15]([NH:27]C(OCC3C=CC=CC=3)=O)[C:14]1=[O:38])=[O:11])[CH2:2]2.C([O-])=O>CO.[Pd]>[NH2:27][CH:15]1[N:16]=[C:17]([CH:24]([CH3:25])[CH3:26])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:13]([CH2:12][C:10]([N:3]2[CH2:2][CH:1]3[CH2:7][CH2:6][CH:5]([CH2:8][CH2:9]3)[CH2:4]2)=[O:11])[C:14]1=[O:38]

Participants

5

Reactant 2

HCID 283FormateHCID 54424633HCID 54424633, compound

Product 1

HCID 53887049HCID 53887049, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd—C (5 wt %, 0.10 g) was added to a suspension of (3RS)-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-3-benzyloxycarbonylamino-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one (0.718 g) in methanol (20 ml) and then anmonium formate (0.351 g) at room temperature. The mixture was stirred at the same condition for 4 hours and filtered on Celite® to remove the catalyst. The filtrate was concentrated in vacuo and the residue was taken up with ethyl acetate (100 ml) and a saturated aqueous sodium hydrogen carbonate (50 ml). The organic layer was washed with a brine (50 ml) and dried over anhydrous sodium sulfate. Filtration and evaporation gave (3RS)-3-amino-1-[(3-azabicyclo[3.2.2]non-3-yl)carbonylmethyl]-2,3-dihydro-5-isopropyl-1H-1,4-benzodiazepin-2-one (0.39 g) which was used in a following reaction step without further purification.

Workup

  1. customat room temperature
  2. filtrationfiltered on Celite®
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated in vacuo
  5. washThe organic layer was washed with a brine (50 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-acf002419e41499fae4d5dea647e27f9
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

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