Tetrabutylammonium Fluoride → 1-[4-(Furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]-3-hydroxyazetidine

HRID 891788Notes

Reaction equation

HRID 891788 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][NH:29][C:30]([C:32]3[O:33][CH:34]=[CH:35][CH:36]=3)=[O:31])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[O:33]1[CH:34]=[CH:35][CH:36]=[C:32]1[C:30]([NH:29][CH2:28][C:26]1[N:27]=[C:23]([N:21]2[CH2:20][CH:19]([OH:18])[CH2:22]2)[S:24][CH:25]=1)=[O:31]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 222429493-t-Butyldiphenylsilyloxy-1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]azetidine

Product 1

HCID 222430041-[4-(Furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]-3-hydroxyazetidineYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-[4-(furan-2-carbonyl-amino)methyl-1,3-thiazol-2-yl]azetidine (1.90 g, 3.68 mmol) (obtained as described in Reference Example 67(1)) in anhydrous tetrahydrofuran (95 ml) was added a solution of 1.0 M tetra-n-butylammonium fluoride in tetrahydrofuran (4.41 ml, 4.41 mmol) in an ice bath and the mixture was stirred in an ice bath for 1 hour. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (10:1) as the eluant to afford 1-[4-(furan-2-carbonylamino)methyl-1,3-thiazol-2-yl]-3-hydroxyazetidine (426 mg, yield 47%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-a1e386346a744cab927dc382fef873dc
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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