Acetic Acid → HCID 22243002, compound

HRID 891571Notes

Reaction equation

HRID 891571 reaction equation
[Si]([O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[S:16][CH:17]=[C:18]([C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[O:21])[N:19]=2)[CH2:11][CH2:10]1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[N+:30]([C:27]1[CH:28]=[CH:29][C:24]([CH2:23][O:22][C:20]([C:18]2[N:19]=[C:15]([N:12]3[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH2:11]3)[S:16][CH:17]=2)=[O:21])=[CH:25][CH:26]=1)([O-:32])=[O:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 22243054HCID 22243054, compound

Product 1

HCID 22243002HCID 22243002, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-t-butyldimethylsilyloxy-1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)piperidine (300 mg, 0.628 mmol) (obtained as described in Reference Example 14(3)) in anhydrous tetrahydrofuran (15 ml) were added acetic acid (0.22 ml, 0.628 mmol) and a solution of 1M tetrabutylammonium fluoride in tetrahydrofuran (3.76 ml, 3.76 mmol) in an ice bath, and the mixture was then stirred at room temperature for 21 hours. After checking the completion of the reaction, the reaction 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 obtained residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (10:1) as the eluant to afford 1-(4-p-nitrobenzyloxycarbonyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (123 mg, yield 54%) as a pale yellow solid.

Workup

  1. customthe completion of the reaction
  2. customthe reaction 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 obtained residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-a6c918f448e843b3be7a2e2e84a1454e
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…