benzyl (3R,5S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate → HCID 67010477, compound

HRID 1630280Notes

Reaction equation

HRID 1630280 reaction equation
[N:1]1([CH2:6][C:7]([N:9]2[C@H:13]([C:14](=[O:30])[NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]4[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=4)=[CH:18][CH:17]=3)[CH2:12][C@@H:11]([NH:31]C(=O)OCC3C=CC=CC=3)[CH2:10]2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1>[Pd].CO>[N:1]1([CH2:6][C:7]([N:9]2[CH2:10][C@H:11]([NH2:31])[CH2:12][C@H:13]2[C:14]([NH:15][C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)=[CH:20][CH:21]=2)=[O:30])=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 86659490benzyl (3R,5S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate

Product 1

HCID 67010477HCID 67010477, compoundYield 157.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask charged with benzyl (3R,5S)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-5-(4-(4-fluorophenoxy)phenylcarbamoyl)pyrrolidin-3-ylcarbamate (1.20 g, 2.15 mmol), prepared as in Example 1, palladium on carbon (10%, 120 mg) and methanol (20 mL) and the mixture was placed under a hydrogen atmosphere (balloon). The mixture was stirred for 2 hours at ambient temperature, filtered and concentrated to give (2S,4R)-1-(2-(1H-1,2,4-triazol-1-yl)acetyl)-4-amino-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (1.44 g, 3.39 mmol), which was carried forward without further purification.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-75be097764b1404b95f2ff62f93ee222
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…