Sulfuric Acid → HCID 53857518, compound

HRID 482248Notes

Reaction equation

HRID 482248 reaction equation
[Br:1][C@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].[CH3:10][C:11]([CH3:13])=[CH2:12].S(=O)(=O)(O)O>C(Cl)Cl>[C:11]([O:4][C:3](=[O:5])[C@H:2]([Br:1])[CH2:6][CH:7]([CH3:9])[CH3:8])([CH3:13])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 12697060(2R)-2-bromo-4-methylpentanoic acid

Product 1

HCID 53857518HCID 53857518, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

33 g of 2(R)-bromo-4-methylpentanoic acid (prepared from D-leucine) was dissolved in 100 ml of methylene chloride. To this solution, at -40° C. was introduced 47 g of 2-methylpropene while stirring, and after the addition of 0.8 ml of sulfuric acid the mixture was stirred overnight at room temperature. The reaction mixture was concentrated to 1/2 in vacuo and washed with 10% sodium carbonate aqueous solution and dried over anhydrous magnesium sulfate. The solution was then evaporated in vacuo, yielding 37.4 g of 2(R)-bromo-4-methylpentanoic acid t-butyl ester.

Workup

  1. stirringwas stirred overnight at room temperature
  2. concentrationThe reaction mixture was concentrated to 1/2 in vacuo
  3. washwashed with 10% sodium carbonate aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solution was then evaporated in vacuo

Sources & evidence

ORD record
ord-672881d697d74e1d99a20a22eb0404e6
Source dataset
uspto-grants-1998_08
Patent number
US05795891

Reaction notes

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