Acetic Acid → tert-Butyl (S)-1-(5-(3-(methylamino)-4-aminophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

HRID 2075313Notes

Reaction equation

HRID 2075313 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:12]2[S:16][C:15]([N:17]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:18][C@@H:19]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:14][N:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.O.C(O)(=O)C>CO.[Pd]>[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([C:12]2[S:16][C:15]([N:17]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:18][C@@H:19]([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=3)=[N:14][N:13]=2)[CH:6]=[CH:7][C:8]=1[NH2:9]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 57991929tert-Butyl (S)-1-(5-(3-(methylamino)-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Product 1

HCID 57991892tert-Butyl (S)-1-(5-(3-(methylamino)-4-aminophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The above mentioned tert-butyl (S)-1-(5-(3-(methylamino)-4-nitrophenyl)-1,3,4-thiadiazol-2-yl-boc-amino)-3-(4-(trifluoromethyl)phenyl)propan-2-ylcarbamate (1.13 g, 2 mmol) was dissolved in 200 mL MeOH in a 500 mL round bottle flask. To this flask, was added 10% Pd/C 100 mg pre-wet with water and 2 mL acetic acid. The mixture was stirred under an atmosphere of hydrogen under balloon pressure for 1 hour. After filtration through a pad of celite, the solution was evaporated to dryness. The residue was re-dissolved in 200 mL of EtOAc. The solution was washed with saturated sodium bicarbonate three times and dried over sodium sulfate. The product was obtained after removing the solvent. It was used directly in the next step.

Workup

  1. filtrationAfter filtration through a pad of celite
  2. customthe solution was evaporated to dryness
  3. dissolutionThe residue was re-dissolved in 200 mL of EtOAc
  4. washThe solution was washed with saturated sodium bicarbonate three times
  5. dry with materialdried over sodium sulfate
  6. customThe product was obtained
  7. customafter removing the solvent

Sources & evidence

ORD record
ord-9446b5df38fe47c2b72afdb0ac488701
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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