Acetic Acid → HCID 22243027, compound

HRID 891740Notes

Reaction equation

HRID 891740 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:46])[NH:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=3)=[O:34])[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[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:46])[NH:29][CH2:30][CH2:31][NH:32][C:33]([O:35][CH2:36][C:37]3[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=3)=[O:34])[N:27]=2)[CH2:20]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 22242944HCID 22242944, compound

Product 1

HCID 22243027HCID 22243027, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[2-(p-nitrobenzyloxycarbonylamino)-ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (1.21 g, 1.84 mmol) (obtained as described in Reference Example 56(4)) in anhydrous tetrahydrofuran (60.6 ml) were added successively acetic acid (0.13 ml, 2.27 mmol) and a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (2.2 ml, 2.2 mmol) in an ice bath. The mixture was stirred for 2.5 hours under the same conditions. 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. To the residue was added isopropyl ether, and the mixture was stirred, washed and filtered off to give 3-hydroxy-1-{4-[2-(p-nitrobenzyloxycarbonylamino)-ethylcarbamoyl]-1,3-thiazol-2-yl}azetidine (667 mg, yield 86%) as a 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. additionTo the residue was added isopropyl ether
  8. stirringthe mixture was stirred
  9. washwashed
  10. filtrationfiltered off

Sources & evidence

ORD record
ord-35b6ea5afa34461cadded7a8fda9b71f
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…