Dichloromethane → (S)-2-amino-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-3-(tetrahydropyran-2-yl)-propionamide hydrochloride

HRID 19033Notes

Reaction equation

HRID 19033 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:16](=[O:28])[NH:17][C:18]1[CH:22]=[CH:21][N:20]([CH2:23][C:24]([OH:27])([CH3:26])[CH3:25])[N:19]=1)[CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)(C)(C)C.FC(F)(F)C(O)=O.[Cl:37]CCl>>[ClH:37].[NH2:7][C@@H:8]([CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][O:11]1)[C:16]([NH:17][C:18]1[CH:22]=[CH:21][N:20]([CH2:23][C:24]([OH:27])([CH3:25])[CH3:26])[N:19]=1)=[O:28]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66899689[(S)-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-2-(tetrahydro-pyran-2-yl)-ethyl]-carbamic acid t-butyl ester

Product 1

HCID 67504601(S)-2-amino-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-3-(tetrahydropyran-2-yl)-propionamide hydrochloride

Procedure

To a solution of [(S)-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-2-(tetrahydro-pyran-2-yl)-ethyl]-carbamic acid t-butyl ester (570 mg) in dichloromethane (3 mL) was added trifluoroacetic acid (3 mL). The mixture was stirred at room temperature for 30 min. Solvents were evaporated and the residue was dried in vacuo. The waxy solid was dissolved in a methanolic hydrogen chloride solution. Solvents were evaporated and the residue was dried in vacuo. The white solid was triturated with diethyl ether and filtered to afford (S)-2-amino-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-3-(tetrahydropyran-2-yl)-propionamide hydrochloride (529 mg). LR-ES-MS m/z calculated for C15H26N4O3 310 [M]+, observed [M+H]+ 311.

Workup

  1. customSolvents were evaporated
  2. customthe residue was dried in vacuo
  3. dissolutionThe waxy solid was dissolved in a methanolic hydrogen chloride solution
  4. customSolvents were evaporated
  5. customthe residue was dried in vacuo
  6. customThe white solid was triturated with diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-16d60f5e007946408bfde3d22cc2d899
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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