Tetrabutylammonium Fluoride → HCID 10288269, compound

HRID 1182130Notes

Reaction equation

HRID 1182130 reaction equation
C([SiH2][O:6][C:7](C1C=CC=CC=1)(C1C=CC=CC=1)[C@@H:8]([NH:24][C:25]([NH:27][C:28]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[CH:29]=1)=[O:26])[CH2:9][CH2:10][N:11]1[CH2:14][CH:13]([C:15](=[O:23])[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH2:12]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([NH:27][C:25]([NH:24][C@H:8]([CH2:7][OH:6])[CH2:9][CH2:10][N:11]2[CH2:12][CH:13]([C:15](=[O:23])[C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)[CH2:14]2)=[O:26])[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131726653HCID 131726653, compound

Product 1

HCID 10288269HCID 10288269, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-{(S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-[3-(4-fluoro-benzoyl)-azetidin-1-yl]-propyl}-3-(3,5-dimethoxy-phenyl)-urea (0.862 g, 0.126 mmol) in THF (3 ml) is treated with a 1 M solution of tetrabutyl ammonium fluoride (TBAF, 0.126 ml), and the reaction mixture stirred at ambient temperature for 2 hours. The reaction mixture is partitioned between ethylacetate and saturated NaHCO3 solution. The ethylacetate phase is washed with water and brine, dried over MgSO4 and evaporated. The crude product is purified by flash silica chromatography (elution with a 5:95 methanol/dichloromethane) to afford 1-(3,5-dimethoxy-phenyl)-3-{(S)-3-[3-(4-fluoro-benzoyl)-azetidin-1-yl]-1-hydroxymethyl-propyl}-urea.

Workup

  1. customThe reaction mixture is partitioned between ethylacetate and saturated NaHCO3 solution
  2. washThe ethylacetate phase is washed with water and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude product is purified by flash silica chromatography (
  6. washelution with a 5:95 methanol/dichloromethane)

Sources & evidence

ORD record
ord-0e97fc430a044bb3bd67764cf7bc4274
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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