Tetrabutylammonium Fluoride → HCID 22242865, compound

HRID 891677Notes

Reaction equation

HRID 891677 reaction equation
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:51])[N:29]([CH2:31][CH2:32][O:33][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:30])[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[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([C:28](=[O:51])[N:29]([CH2:31][CH2:32][OH:33])[CH3:30])[N:27]=2)[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22243008HCID 22243008, compound

Product 1

HCID 22242865HCID 22242865, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-{N-[2-(t-butyldiphenylsilyloxy)ethyl]-N-methyl-carbamoyl}-1,3-thiazol-2-yl)azetidine (2.24 g, 3.05 mmol) (obtained as described in Reference Example 40(2)) in anhydrous tetrahydrofuran (70 ml) was added a solution of 1.0M tetra-n-butylammonium fluoride in tetrahydrofuran (7.32 ml, 7.32 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 concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (20:1)→ethyl acetate:methanol (15:1) as the eluant to afford 3-hydroxy-1-{4-[N-(2-hydroxyethyl)-N-methyl-carbamoyl]-1,3-thiazol-2-yl}azetidine (833 mg, yield 94%) 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-cfaeb72ca7da45aca4d548d53309999c
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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