Hydrochloric Acid → (S)-3-(2,3-difluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea

HRID 340963Notes

Reaction equation

HRID 340963 reaction equation
[Si]([O:8][CH2:9][C@@H:10]([N:14]([CH3:27])[C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:20]=1[F:26])=[O:16])[CH2:11][CH:12]=[CH2:13])(C(C)(C)C)(C)C.Cl>CO>[F:26][C:20]1[C:21]([F:25])=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:15](=[O:16])[N:14]([C@@H:10]([CH2:11][CH:12]=[CH2:13])[CH2:9][OH:8])[CH3:27]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57947466(S)-1-(1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl)-3-(2,3-difluorobenzyl)-1-methylurea

Product 1

HCID 57948061(S)-3-(2,3-difluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylureaYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-1-(1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl)-3-(2,3-difluorobenzyl)-1-methylurea (3.45 g, 8.65 mmol) in MeOH (60 mL) was added HCl (4 N in dioxane, 11.0 mL). The resulting solution was stirred at RT for 30 min. The mixture was concentrated and re-dissolved in EtOAc. The organic mixture was washed with saturated NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give (S)-3-(2,3-difluorobenzyl)-1-(1-hydroxypent-4-en-2-yl)-1-methylurea (2.5 g, quant.) as a white solid, which was used without further purification. LRMS (M+H+) m/z 285.2.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionre-dissolved in EtOAc
  3. washThe organic mixture was washed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-724a97e6ff1b42b7aa02214b2157da4f
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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