Tetrabutylammonium Fluoride → 3-Hydroxy-1-(4-phenylcarbamoyl-1,3-thiazol-2-yl)azetidine

HRID 891620Notes

Reaction equation

HRID 891620 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:36])[NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[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:36])[NH:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:27]=2)[CH2:22]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22242939HCID 22242939, compound

Product 1

HCID 222430413-Hydroxy-1-(4-phenylcarbamoyl-1,3-thiazol-2-yl)azetidineYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-phenylcarbamoyl-1,3-thiazol-2-yl)azetidine (2.20 g, 4.29 mmol) (obtained as described in Reference Example 32(1)) in anhydrous tetrahydrofuran (110 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (5.15 ml, 5.15 mmol) in an ice bath, and then the mixture was stirred 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 ethyl acetate as the eluant to afford 3-hydroxy-1-(4-phenylcarbamoyl-1,3-thiazol-2-yl)azetidine (1.18 g, yield 100%) 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-0363404b4c1a40a0b4ac5095d21dd553
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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