Ammonium formate → HCID 15887031, compound

HRID 382469Notes

Reaction equation

HRID 382469 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH2:17][C@H:18]([N:20]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH2:38][CH3:39])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH3:19])[CH:7]=[C:8]2[C:12]=1[N:11]([CH2:13][CH2:14][CH2:15][OH:16])[CH2:10][CH2:9]2)(=[O:3])[NH2:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([C:4]1[CH:5]=[C:6]([CH2:17][C@H:18]([N:20]([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[O:37][CH2:38][CH3:39])[C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:24])[CH3:25])[CH3:19])[CH:7]=[C:8]2[C:12]=1[N:11]([CH2:13][CH2:14][CH2:15][OH:16])[CH:10]=[CH:9]2)(=[O:3])[NH2:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12074057HCID 12074057, compound

Product 1

HCID 15887031HCID 15887031, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxy-propyl)-2,3-dihydro-1H-indol-5-yl]-1-methylethyl]-N-[2-(2-ethoxyphenoxy)ethyl]carbamate (4.93 g) was dissolved in methanol (150 ml), and 10% palladium on carbon (490 mg) and ammonium formate (2.96 g) were added to the solution. After the mixture was heated under reflux for 36 hours and cooled, the insoluble material was filtered off. The solvent was removed in vacuo, and the residue was dissolved in methanol (150 ml). 10% Palladium on carbon (490 mg) and ammonium formate (2.96 g) were added to the solution. After the mixture was heated under reflux for 24 hours and cooled, the insoluble material was filtered off. The filtrate was concentrated in vacuo, and the residue was dissolved in ethyl acetate. The solution was washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo to give white amorphous tert-butyl (R)-N-[2-[7-carbamoyl-1-(3-hydroxypropyl)-1H-indol-5-yl]-1-methylethyl]-N-[2-(2-ethoxyphenoxy)ethyl]-carbamate (4.55 g).

Workup

  1. temperatureAfter the mixture was heated
  2. temperatureunder reflux for 36 hours
  3. temperaturecooled
  4. filtrationthe insoluble material was filtered off
  5. customThe solvent was removed in vacuo
  6. dissolutionthe residue was dissolved in methanol (150 ml)
  7. addition10% Palladium on carbon (490 mg) and ammonium formate (2.96 g) were added to the solution
  8. temperatureAfter the mixture was heated
  9. temperatureunder reflux for 24 hours
  10. temperaturecooled
  11. filtrationthe insoluble material was filtered off
  12. concentrationThe filtrate was concentrated in vacuo
  13. dissolutionthe residue was dissolved in ethyl acetate
  14. washThe solution was washed with water and brine
  15. dry with materialdried over anhydrous sodium sulfate
  16. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-03f9cd39153347d4a1cde230a47b4246
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

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