Trifluoroacetic acid → HCID 66818016, compound

HRID 1755137Notes

Reaction equation

HRID 1755137 reaction equation
C(O[C:6](=O)[N:7]([C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][CH2:17][S:18]([N:21]2[CH2:37][CH2:36][C:24]3([N:28]=[C:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=[CH2:34])[NH:26][C:25]3=[O:35])[CH2:23][CH2:22]2)(=[O:20])=[O:19])=[C:11]([CH3:38])[CH:10]=1)C)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:15][C:13]1[CH:14]=[C:9]([NH:7][CH3:6])[CH:10]=[C:11]([CH3:38])[C:12]=1[CH2:16][CH2:17][S:18]([N:21]1[CH2:22][CH2:23][C:24]2([N:28]=[C:27]([CH2:29][CH2:30][CH2:31][CH2:32][CH:33]=[CH2:34])[NH:26][C:25]2=[O:35])[CH2:36][CH2:37]1)(=[O:19])=[O:20]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66817764HCID 66817764, compound

Product 1

HCID 66818016HCID 66818016, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{4-[2-(2-Hex-5-enyl-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl)-ethyl]-3,5-dimethyl-phenyl}-methyl-carbamic acid tert-butyl ester (820 mg, 1.46 mmol) was dissolved in methylene chloride (16 ml). Trifluoroacetic acid (10 ml) was added and the mixture was stirred at room temperature for two hours. The reaction solution was concentrated, and a saturated aqueous sodium bicarbonate solution was added to the residue. This mixture was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give 8-[2-(2,6-dimethyl-4-methylamino-phenyl)-ethanesulfonyl]-2-hex-5-enyl-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (686 mg) as a crude compound.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiona saturated aqueous sodium bicarbonate solution was added to the residue
  3. extractionThis mixture was extracted with methylene chloride
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-051a62368c9d4675b0d01f57b504ac58
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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