Hydrochloric Acid → HCID 58734243, compound

HRID 2080527Notes

Reaction equation

HRID 2080527 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][S:6]([NH:9][C:10]1[CH:15]=[C:14]([CH:16]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[C:13]([Cl:35])=[CH:12][N:11]=1)(=[O:8])=[O:7])C.O.[OH-].[Li+].Cl.FC(F)(F)C(O)=O>O1CCCC1.O.C(Cl)Cl.CO>[Cl:35][C:13]1[C:14]([CH:16]([S:25]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])=[CH:15][C:10]([NH:9][S:6]([CH2:5][C:4]([OH:36])=[O:3])(=[O:8])=[O:7])=[N:11][CH:12]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 168937Lithium hydroxide, monohydrateHCID 58734245HCID 58734245, compound

Product 1

HCID 58734243HCID 58734243, compoundYield 94.2%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the ethyl[[[5-chloro-4-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-2-yl]amino]sulfonyl]acetate (60 mg, 0.104 mmol) obtained in Example 283 in a mixture of tetrahydrofuran (5 ml) and water (1 ml) was added lithium hydroxide monohydrate (9.1 mg, 0.218 mmol). The resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 1N hydrochloric acid. The resulting mixture was extracted with methylene chloride. The extract was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography. The fraction obtained from the methanol:methylene chloride (=1:30) eluate containing 0.5% trifluoroacetic acid was concentrated under reduced pressure to give the title compound (54 mg, 0.098 mmol, 94%) as a white solid.

Workup

  1. extractionThe resulting mixture was extracted with methylene chloride
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue thus obtained
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-4306c06b66e54fdb8d8cdfaff6fafe9f
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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