Sulfuric Acid → HCID 54289398, compound

HRID 2228306Notes

Reaction equation

HRID 2228306 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].S(=O)(=O)(O)O.[CH2:12]([O:19][C:20]([CH:22]([NH:28][CH3:29])[CH2:23][CH2:24][C:25]([OH:27])=[O:26])=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+]>C(O)(C)(C)C.ClCCl>[CH2:12]([O:19][C:20]([CH:22]([NH:28][CH3:29])[CH2:23][CH2:24][C:25]([O:27][C:13]([CH3:18])([CH3:14])[CH3:12])=[O:26])=[O:21])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 24083Sulfuric acid magnesium salt (1:1)2×HCID 516892Sodium BicarbonateHCID 18472650HCID 18472650, compound

Product 1

HCID 54289398HCID 54289398, compoundYield 106.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

To dichloromethane (1000 ml) was added at room temperature anhydrous magnesium sulfate (50.6 g) and then concentrated sulfuric acid (6.0 ml). The mixture was stirred at room temperature for 15 minutes, and to the mixture was added 4-[(benzyloxy)carbonyl]−4-methylaminobutyric acid (26.3 g) and then tert-butanol (50.5 ml). The mixture was sealed completely and stirred at room temperature for 18 hours. To the mixture was added saturated sodium hydrogen carbonate solution to dissolve all of the magnesium sulfate, and the mixture was stirred. The organic layer was separated, washed with saturated brine (400 ml) and dried with anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified with silica gel column chromatography (250 g, hexane:ethyl acetate=5:1) to give tert-butyl 4-[(benzyloxy)-carbonyl]−4-methylaminobutyrate (17.2 g, 53%).

Workup

  1. customThe mixture was sealed completely
  2. stirringstirred at room temperature for 18 hours
  3. stirringthe mixture was stirred
  4. customThe organic layer was separated
  5. washwashed with saturated brine (400 ml)
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified with silica gel column chromatography (250 g, hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-0c187d91e8b14c859fd8c2ca9573c3c7
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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