Citric Acid → HCID 66816147, compound

HRID 1755020Notes

Reaction equation

HRID 1755020 reaction equation
C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C([Si](C)(C)[O:19][CH2:20][CH2:21][N:22]([C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[S:35]([N:38]2[CH2:59][CH2:58][C:41]3([N:45]=[C:44]([C:46]4[CH:51]=[CH:50][CH:49]=[C:48]([O:52][C:53]([F:56])([F:55])[F:54])[CH:47]=4)[NH:43][C:42]3=[O:57])[CH2:40][CH2:39]2)(=[O:37])=[O:36])=[C:29]([CH3:60])[CH:28]=1)[S:23]([CH3:26])(=[O:25])=[O:24])(C)(C)C>C(#N)C.C(OCC)(=O)C>[OH:19][CH2:20][CH2:21][N:22]([C:27]1[CH:32]=[CH:31][C:30](/[CH:33]=[CH:34]/[S:35]([N:38]2[CH2:39][CH2:40][C:41]3([N:45]=[C:44]([C:46]4[CH:51]=[CH:50][CH:49]=[C:48]([O:52][C:53]([F:54])([F:55])[F:56])[CH:47]=4)[NH:43][C:42]3=[O:57])[CH2:58][CH2:59]2)(=[O:37])=[O:36])=[C:29]([CH3:60])[CH:28]=1)[S:23]([CH3:26])(=[O:24])=[O:25]

Participants

5

Reactant 2

HCID 311Citric AcidHCID 66817536HCID 66817536, compound

Product 1

HCID 66816147HCID 66816147, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A 10% aqueous citric acid solution (0.14 ml, 0.067 mmol) was added to a solution of N-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-N-(3-methyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-methanesulfonamide (14.3 mg, 0.0192 mmol) in acetonitrile (0.2 ml), and the mixture was stirred at 60° C. for 2.5 hours. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with an aqueous sodium bicarbonate solution, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate) to give N-(2-hydroxy-ethyl)-N-(3-methyl-4-{(E)-2-[4-oxo-2-(3-trifluoromethoxy-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-vinyl}-phenyl)-methanesulfonamide (12.5 mg, 100%).

Workup

  1. washthe organic layer was washed with an aqueous sodium bicarbonate solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-e4c41f038cc344d1a6d7ba6010f6f73f
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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