Tetrabutylammonium Fluoride → HCID 22243076, compound

HRID 891776Notes

Reaction equation

HRID 891776 reaction equation
[C:1]([NH:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]2[CH2:19][CH:18]([O:20][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:17]2)[S:14][CH:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([NH:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]2[CH2:17][CH:18]([OH:20])[CH2:19]2)[S:14][CH:15]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22242952HCID 22242952, compound

Product 1

HCID 22243076HCID 22243076, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1-[4-(benzoylaminomethyl)-1,3-thiazol-2-yl]-3-t-butyldiphenylsilyloxyazetidine (1.49 g, 2.82 mmol) (obtained as described in Reference Example 64(1)) in anhydrous tetrahydrofuran (75 ml) was added a 1.0 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (3.39 ml, 3.39 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 hexane:ethyl acetate (1:2) ethyl acetate:methanol (9:1) as the eluant to afford 1-[4-(benzoylaminomethyl)-1,3-thiazol-2-yl]-3-hydroxyazetidine (582 mg, yield 71%) 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-562247d0edf64969bc9f32ea2e9bd27f
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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