Trifluoroacetic acid → (S)-2-amino-3-cyclohexyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide trifluoroacetate

HRID 18990Notes

Reaction equation

HRID 18990 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][CH2:11]1)(C)(C)C.[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33]>ClCCl>[F:30][C:31]([F:36])([F:35])[C:32]([OH:34])=[O:33].[NH2:7][C@@H:8]([CH2:9][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]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 2

HCID 6422Trifluoroacetic acidHCID 66899112HCID 66899112, compound

Product 1

HCID 67504359(S)-2-amino-3-cyclohexyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide trifluoroacetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {(S)-2-cyclohexyl-1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-ethyl}-carbamic acid t-butyl ester (0.61 g 1.5 mmol) in dichloromethane (10 mL) was treated with trifluoroacetic acid (5 mL). The mixture was stirred at room temperature for 0.5 h, and concentrated to afford (S)-2-amino-3-cyclohexyl-N-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-yl]-propionamide trifluoroacetate (630 mg, 100%) as a white solid.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-ed2503d0e59c40cbb4787388917fedd9
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Reaction notes

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