Trifluoroacetic acid → HCID 67482613, compound

HRID 719898Notes

Reaction equation

HRID 719898 reaction equation
C([O:5][C:6]([C:8]1[CH:13]=[N:12][C:11]([NH:14][C:15](=[O:34])[C@@H:16]([C:23]2[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[C:25]([Cl:33])[CH:24]=2)[CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:10][N:9]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:33][C:25]1[CH:24]=[C:23]([C@@H:16]([CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[C:15]([NH:14][C:11]2[N:12]=[CH:13][C:8]([C:6]([OH:7])=[O:5])=[N:9][CH:10]=2)=[O:34])[CH:28]=[CH:27][C:26]=1[S:29]([CH3:32])(=[O:31])=[O:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67482855HCID 67482855, compound

Product 1

HCID 67482613HCID 67482613, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid tert-butyl ester (3.29 g, 6.48 mmol) in methylene chloride (30 mL) was treated with trifluoroacetic acid (60 mL) and stirred at 25° C. for 65 min. The reaction solution was then concentrated in vacuo The resulting oil was diluted with ethyl acetate (500 mL), washed with water (2×250 mL) and a saturated aqueous sodium chloride solution (5×250 mL), dried over sodium sulfate, treated with decolorizing carbon, filtered through a pad of celite, and concentrated in vacuo to afford the 5-[2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionylamino]-pyrazine-2-carboxylic acid (2.89 g, 99%) as a light yellow foam: mp 121–127° C.; (ES)+-HRMS m/e calcd for C20H22ClN3O5S (M+H)+ 452.1042, found 452.1046. This material was used without further purification.

Workup

  1. concentrationThe reaction solution was then concentrated in vacuo The resulting oil
  2. additionwas diluted with ethyl acetate (500 mL)
  3. washwashed with water (2×250 mL)
  4. dry with materiala saturated aqueous sodium chloride solution (5×250 mL), dried over sodium sulfate
  5. additiontreated with decolorizing carbon
  6. filtrationfiltered through a pad of celite
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3aece2f2a4c425aa01055e9bcc9d964
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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