Trifluoroacetic acid → HCID 178469367, compound

HRID 1242868Notes

Reaction equation

HRID 1242868 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([O:11]CC2C=CC(OC)=CC=2)[N:8]([CH2:21][C:22](=[O:38])[NH:23][C@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:7]=1)=[O:5])[CH3:2].FC(F)(F)C(O)=O>O>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([OH:11])[N:8]([CH2:21][C:22](=[O:38])[NH:23][C@H:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]2[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 58646713HCID 58646713, compound

Product 1

HCID 178469367HCID 178469367, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An ice cold sample of 100 mg (0.192 mmol) of 1-[((1S, 2S)2-Benzyloxy-cyclohexylcarbamoyl)-methyl]-5-(4-methoxy-benzyloxy)-1H-pyrazole-3-carboxylic acid ethyl ester (2) was treated with 5 mL of 95:5 trifluoroacetic acid (TFA):H2O solution, and the resulting mixture was stirred for 1.5 h at rt, and then quenched by the addition of 5 mL of 1:1 acetonitrile:water solution. The mixture was concentrated to give 66 mg (86%) of crude 1-[((1S, 2S)2-benzyloxy-cyclohexylcarbamoyl)-methyl]-5-hydroxy-1H-pyrazole-3-carboxylic acid ethyl ester (3) which was used without any further purification in the next reaction.

Workup

  1. customquenched by the addition of 5 mL of 1:1 acetonitrile
  2. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-8ef6a4a29a414b16a988fd0b9f979ceb
Source dataset
uspto-grants-2006_10
Patent number
US07115749B2

Reaction notes

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