Acetic Acid → HCID 22242963, compound

HRID 891705Notes

Reaction equation

HRID 891705 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:47])[N:29]([CH:44]([CH3:46])[CH3:45])[CH2:30][C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=3)=[O:32])[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:47])[N:29]([CH:44]([CH3:45])[CH3:46])[CH2:30][C:31]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][CH:36]=3)=[O:32])[N:27]=2)[CH2:20]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 22242753HCID 22242753, compound

Product 1

HCID 22242963HCID 22242963, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-{4-[N-isopropyl-N-(p-nitrobenzyloxycarbonylmethyl)carbamoyl]-1,3-thiazol-2-yl}azetidine (1.81 g, 2.69 mmol) (obtained as described in Reference Example 48(4)) in anhydrous tetrahydrofuran (90 ml) were added acetic acid (0.18 ml, 3.23 mmol) and a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (3.23 ml, 3.23 mmol) in an ice bath. The mixture was stirred in the ice bath for 2 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using methylene chloride:ethyl acetate (1:1) as the eluant to afford 3-hydroxy-1-{4-[N-isopropyl-N-(p-nitrobenzyloxycarbonylmethyl)carbamoyl]-1,3-thiazol-2-yl}azetidine (968 mg, yield 83%) as a white solid.

Workup

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-17cea7fdf69c4b7dab9ca1c36d5586b6
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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