Water → HCID 86669564, compound

HRID 524439Notes

Reaction equation

HRID 524439 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:42]=[CH:43][CH:44]=1)[O:13][C:14]1[S:18][C:17]([NH:19][C:20](=[O:41])[CH:21]([C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH:38]3[CH2:40][CH2:39]3)(=[O:37])=[O:36])=[CH:31][CH:30]=2)[O:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:16][CH:15]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C(OCC)(=O)C>C1COCC1>[CH:38]1([S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH:21]([O:22][CH:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[C:20]([NH:19][C:17]3[S:18][C:14]([O:13][C:12]4[CH:42]=[CH:43][CH:44]=[C:10]([CH2:9][OH:8])[CH:11]=4)=[CH:15][N:16]=3)=[O:41])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86669565HCID 86669565, compound

Product 1

HCID 86669564HCID 86669564, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[5-[3-[[tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]thiazol-2-yl]-2-(4-cyclopropylsulfonylphenyl)-2-tetrahydropyran-4-yloxy-acetamide (0.05 g, 0.0758 mmol) was taken in 3 mL of dry THF and to it tetra-n-butylammonium fluoride (0.16 mL, 0.16 mmol, 1M solution in THF) was added in inert atmosphere at 0° C. After complete addition the reaction was stirred for overnight at room temperature. TLC showed complete reaction. The reaction mixture was portioned between water and ethyl acetate. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed on vacuo to get the crude product which was purified by preparative TLC to get the solid product (0.020 g).

Workup

  1. additionwas added in inert atmosphere at 0° C
  2. additionAfter complete addition the reaction
  3. customreaction
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed on vacuo
  8. customto get the crude product which
  9. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-7fe290365e8c4694aab1c47ab15f287b
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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