2,2-Dimethoxypropane → 3-(2-Chloro-3-fluorobenzyl)-1-methylurea
Reaction equation
[Si](OC[C@@H:10]([N:16](C)[C:17]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[Cl:28])=[O:18])C[C@@H](O)CO)(C(C)(C)C)(C)C.COC(OC)(C)C.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Cl:28][C:22]1[C:23]([F:27])=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][NH:19][C:17](=[O:18])[NH:16][CH3:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of the 1-((2S,4R)-1-(tert-butyldimethylsilyloxy)-4,5-dihydroxypentan-2-yl)-3-(2-chloro-3-fluorobenzyl)-1-methylurea 1(4.5 g, 10.0 mmol) in DMF (170 mL) were added 2,2-dimethoxypropane (12.45 mL, 100.0 mmol) and PPTS (0.050 g, 0.02 mmol) at 0° C. After 1 h the reaction was warmed up to RT and stirred for an additional 2.5 h. The crude reaction mixture was then added into a saturated aqueous solution of NaHCO3 (350 mL) and extracted with EtOAc (3×300 mL). Combined organic layers were washed with Brine (2×400 mL) and dried over MgSO4. The solution was then concentrated to give 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, which was used without further purification. LRMS (M+H+) m/z 490.1.
Workup
- customThe crude reaction mixture
- extractionextracted with EtOAc (3×300 mL)
- washCombined organic layers were washed with Brine (2×400 mL)
- dry with materialdried over MgSO4
- concentrationThe solution was then concentrated
Sources & evidence
- ORD record
- ord-09d5c6f70b824304b8d6182f8934df0d
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088793B2
Reaction notes
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