Hydrochloric Acid → HCID 89963541, compound

HRID 337922Notes

Reaction equation

HRID 337922 reaction equation
[Si]([O:8][C@@H:9]1[CH2:13][C@H:12]([O:14][C:15]2[C:20]([F:21])=[CH:19][C:18]([S:22]([N:25]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][C:34]=3[O:41][CH3:42])[C:26]3[CH:31]=[CH:30][N:29]=[CH:28][N:27]=3)(=[O:24])=[O:23])=[C:17]([F:43])[CH:16]=2)[C@@H:11]([C:44]2[N:48]([CH3:49])[N:47]=[CH:46][CH:45]=2)[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[CH3:42][O:41][C:34]1[CH:35]=[C:36]([O:39][CH3:40])[CH:37]=[CH:38][C:33]=1[CH2:32][N:25]([C:26]1[CH:31]=[CH:30][N:29]=[CH:28][N:27]=1)[S:22]([C:18]1[CH:19]=[C:20]([F:21])[C:15]([O:14][C@H:12]2[CH2:13][C@@H:9]([OH:8])[CH2:10][C@@H:11]2[C:44]2[N:48]([CH3:49])[N:47]=[CH:46][CH:45]=2)=[CH:16][C:17]=1[F:43])(=[O:23])=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 89962902HCID 89962902, compound

Product 1

HCID 89963541HCID 89963541, compoundYield 110.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 4-{[(1S*,2R*,4S*)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(1-methyl-1H-pyrazol-5-yl)cyclopentyl]oxy}-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(pyrimidin-4-yl)benzenesulfonamide (1.25 g, 1.75 mmol) prepared in Example 120b and tetrabutyl ammonium fluoride (1.0 M solution in THF; 5.24 mL, 5.25 mmol) in THF (8.0 mL) was stirred at room temperature for 3 hours. To the reaction solution, 1 M hydrochloric acid (10 mL) was added, followed by extraction with ethyl acetate (100 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (methylene chloride/methanol) to yield the title compound (1.16 g, 99%) as a yellow oil.

Workup

  1. extractionfollowed by extraction with ethyl acetate (100 mL)
  2. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  3. concentrationAfter vacuum concentration
  4. customthe residue was purified with silica gel chromatography (methylene chloride/methanol)

Sources & evidence

ORD record
ord-7205361a1a024b82a9c8896b10e90007
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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