Acetic Acid → HCID 17858109, compound

HRID 891715Notes

Reaction equation

HRID 891715 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:49])[NH:29][CH:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=4)=[O:37])[CH2:32][CH2:31]3)[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:18][CH:19]1[CH2:20][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:49])[NH:29][CH:30]3[CH2:35][CH2:34][N:33]([C:36]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=4)=[O:37])[CH2:32][CH2:31]3)[N:27]=2)[CH2:22]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 69544092HCID 69544092, compound

Product 1

HCID 17858109HCID 17858109, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[1-(p-nitrobenzyloxycarbonyl)-piperidin-4-ylcarbamoyl]-1,3-thiazol-2-yl}azetidine (570 mg, 0.820 mmol) (obtained as described in Reference Example 51(5)) in anhydrous tetrahydrofuran (17 ml) were added successively acetic acid (56 μl, 0.984 mmol) and a 1.0M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (984 μl, 0.984 mmol) in an ice bath, and the mixture was stirred in the ice bath for 1 hour. 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 successively with a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (1:3)→ethyl acetate:methanol (95:5) as the eluant to afford 3-hydroxy-1-{4-[1-(p-nitrobenzyloxycarbonyl)-piperidin-4-ylcarbamoyl]-1,3-thiazol-2-yl}azetidine (360 mg, yield 95%) as a white 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 successively with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium 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-af9383dd02124a77b1395ccfee17c7f2
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…