Ammonium formate → HCID 12074059, compound

HRID 382472Notes

Reaction equation

HRID 382472 reaction equation
[C:1]([O:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:23][C@H:24]([N:26]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH2:37][CH3:38])[CH3:25])=[CH:17][C:18]=2[C:20](=[O:22])[NH2:21])[CH2:13][CH2:12]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:7][CH2:8][CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:23][C@H:24]([N:26]([C:39]([O:41][C:42]([CH3:43])([CH3:44])[CH3:45])=[O:40])[CH2:27][CH2:28][O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[O:36][CH2:37][CH3:38])[CH3:25])=[CH:17][C:18]=2[C:20](=[O:22])[NH2:21])[CH:13]=[CH:12]1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 12074058HCID 12074058, compound

Product 1

HCID 12074059HCID 12074059, compoundYield 96.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(R)-3-[5-[2-[N-(tert-Butoxycarbonyl)-N-[2- (2-ethoxy-phenoxy)ethyl]amino]propyl]-7-carbamoyl-2,3-dihydro-1H-indol-1-yl]propyl pivalate (8.53 g) was dissolved in methanol (280 ml), and 10% palladium on carbon (853 mg) and ammonium formate (3.97 g) were added to the solution. The mixture was heated under reflux for 13 hours, and the catalysts were filtered off. The solvent was removed in vacuo to give pale green amorphous (R)-3-[5-[2-[N-(tert-butoxycarbonyl)-N-[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-7-carbamoyl-1H-indol-1-yl]propyl pivalate (8.20 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 13 hours
  3. filtrationthe catalysts were filtered off
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-43cc74a82d544a758648b00a0e8bc73f
Source dataset
uspto-grants-2001_10
Patent number
US06310086B1

Reaction notes

Loading…