Trifluoroacetic acid → HCID 178499334, compound

HRID 244920Notes

Reaction equation

HRID 244920 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:33]#[C:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:8][C:9]=1[N:10]([C:24]([C@H:26]1[CH2:31][CH2:30][C@H:29]([CH3:32])[CH2:28][CH2:27]1)=[O:25])[CH:11]1[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]1)=[O:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:33]#[C:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[CH:8][C:9]=1[N:10]([C:24]([C@H:26]1[CH2:27][CH2:28][C@H:29]([CH3:32])[CH2:30][CH2:31]1)=[O:25])[CH:11]1[CH2:12][CH2:13][NH:14][CH2:15][CH2:16]1)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178499336HCID 178499336, compound

Product 1

HCID 178499334HCID 178499334, compoundYield 125.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The product from step IV (5.198 g) is dissolved in 30 mL of CH2Cl2 and treated with 20 mL of trifluoroacetic acid. The mixture is stirred at room temperature overnight, then it is evaporated to dryness, obtained residue is redissolved in CH2Cl2 and washed with aqueous NaHCO3 and brine. Organic fraction is separated, dried over Na2SO4, and concentrated to give 5.340 g of crude 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(piperidin-4-yl)amino]-thiophene-2-carboxylic acid methyl ester.

Workup

  1. customit is evaporated to dryness
  2. customobtained residue
  3. washwashed with aqueous NaHCO3 and brine
  4. customOrganic fraction is separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-63dc5649cdcb4fd789e6b57b5b3852ae
Source dataset
uspto-grants-2014_02
Patent number
US08658674B2

Reaction notes

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