Hydrochloric Acid → HCID 66622773, compound

HRID 409828Notes

Reaction equation

HRID 409828 reaction equation
[Si](O[CH2:9][C@@H:10]([N:17]([CH3:30])[C:18]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[C:23]=1[F:29])=[O:19])[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])(C(C)(C)C)(C)C.Cl>CO>[F:29][C:23]1[C:24]([F:28])=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][NH:20][C:18](=[O:19])[N:17]([C@@H:10]([CH3:9])[CH2:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH3:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57947962HCID 57947962, compound

Product 1

HCID 66622773HCID 66622773, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl 5-(tert-butyldimethylsilyloxy)-4-(3-(2,3-difluorobenzyl)-1-methylureido)pentanoate (9.7 g, 21.6 mmol) in MeOH (40 mL) was added HCl (4 N in dioxane, 5.4.0 mL, 21.6 mmol). The resulting solution was stirred at RT for 1 h. 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)-methyl 4-(3-(2,3-difluorobenzyl)-1-methylureido)pentanoate (6.84 g, crude) as a white solid, which was used without further purification. LRMS (M+H+)/m/z 331.2.

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-f257cbfe4c22495b8ebec72f310e212c
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

Loading…