Tetrabutylammonium Fluoride → 3-(2-chloro-3-fluorobenzyl)-1-((S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropan-2-yl)-1-methylurea

HRID 409850Notes

Reaction equation

HRID 409850 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:19]([CH3:32])[C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[C:25]=1[Cl:31])=[O:21])[CH2:11][C@@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:31][C:25]1[C:26]([F:30])=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][NH:22][C:20](=[O:21])[N:19]([C@H:10]([CH2:9][OH:8])[CH2:11][C@@H:12]1[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13]1)[CH3:32]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 579477701-((S)-1-(tert-butyldimethylsilyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea

Product 1

HCID 579475573-(2-chloro-3-fluorobenzyl)-1-((S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropan-2-yl)-1-methylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-((S)-1-(tert-butyldimethylsilyloxy)-3-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)propan-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea (11.4 g, 23 mmol) in THF at 0° C., was added TBAF (23 mmol, 1 equiv.) dropwise. The reaction was completed in 30 min. The solvents were removed. The residue was dissolved in EtOAc (150 mL) and washed with 3% citric acid (150 mL) twice, followed by saturated NaHCO3 (100 mL) and brine (100 mL). The organic layer was concentrated to give 3-(2-chloro-3-fluorobenzyl)-1-((S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-hydroxypropan-2-yl)-1-methylurea, which was used without further purification. LRMS (M+H+) m/z 375.4.

Workup

  1. customThe solvents were removed
  2. dissolutionThe residue was dissolved in EtOAc (150 mL)
  3. washwashed with 3% citric acid (150 mL) twice
  4. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-5595eece04784262a06ade2df1e77ec1
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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