Tetrabutylammonium Fluoride → Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate

HRID 927924Notes

Reaction equation

HRID 927924 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([NH:22][C:23]1[C:32]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[CH2:38][O:39][Si](C(C)(C)C)(C)C)=[CH:31][CH:30]=[C:29]([NH:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[CH3:20]>C1COCC1>[C:19]([NH:22][C:23]1[C:32]([C:33]2[CH:37]=[CH:36][O:35][C:34]=2[CH2:38][OH:39])=[CH:31][CH:30]=[C:29]([NH:47][C:48](=[O:53])[C:49]([CH3:52])([CH3:51])[CH3:50])[C:24]=1[C:25]([O:27][CH3:28])=[O:26])(=[O:21])[CH3:20]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90071968Methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate2×

Product 1

HCID 70984627Methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoateYield 60.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Tetrabutylammonium fluoride (1M solution in THF, 1.1 mL) was added to a stirred, cooled solution of methyl 2-acetylamino-3-[2-(tert-butyldimethylsilanyloxymethyl)-furan-3-yl]-6-(2,2-dimethylpropionylamino)benzoate (Intermediate 34, 0.43 g) in THF (10 mL) at 0° C. and the mixture was stirred at 0° C. for 40 minutes then evaporated to dryness. The residue was partitioned between ethyl acetate and water and the organic layer was washed with brine, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-2% to give methyl 2-acetylamino-6-(2,2-dimethylpropionylamino)-3-(2-hydroxymethylfuran-3-yl)benzoate (0.2 g) as a gum.

Workup

  1. customthen evaporated to dryness
  2. customThe residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on silica eluting with a mixture of methanol and ethyl acetate with a gradient of 0-2%

Sources & evidence

ORD record
ord-a1a9d103046141fd823563acadee9fe4
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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