(S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate → (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-amino-N-(4-(4-fluorophenoxy)phenyl)pentanamide

HRID 1630288Notes

Reaction equation

HRID 1630288 reaction equation
[N:1]1([CH2:6][C:7]([NH:9][C@H:10]([C:25]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)=[CH:30][CH:29]=2)=[O:26])[CH2:11][CH2:12][CH2:13][NH:14]C(=O)OCC2C=CC=CC=2)=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1>[Pd].CO>[N:1]1([CH2:6][C:7]([NH:9][C@@H:10]([CH2:11][CH2:12][CH2:13][NH2:14])[C:25]([NH:27][C:28]2[CH:29]=[CH:30][C:31]([O:34][C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=3)=[CH:32][CH:33]=2)=[O:26])=[O:8])[CH:5]=[N:4][CH:3]=[N:2]1

Participants

4

Reactant 1

HCID 70641275(S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate

Product 1

HCID 67010500(S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-amino-N-(4-(4-fluorophenoxy)phenyl)pentanamideYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Step (a) A flask was charged with (S)-benzyl 4-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-(4-(4-fluorophenoxy)phenylamino)-5-oxopentylcarbamate (700 mg, 1.25 mmol), prepared as in Example 1, palladium on carbon (10%, 70 mg) and methanol (30 mL) and the mixture was placed under a hydrogen atmosphere (balloon). The mixture was stirred 16 hours at ambient temperature and then concentrated and filtered. Product was purified from the residue by reverse phase HPLC to give (S)-2-(2-(1H-1,2,4-triazol-1-yl)acetamido)-5-amino-N-(4-(4-fluorophenoxy)phenyl)pentanamide (420 mg, 0.985 mmol, 79%) as an off-white solid.

Workup

  1. concentrationconcentrated
  2. filtrationfiltered
  3. customProduct was purified from the residue by reverse phase HPLC

Sources & evidence

ORD record
ord-74a70194efd64ae18ce7ac1066be0a26
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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