Ethyl Bromide → HCID 57790784, compound

HRID 2280413Notes

Reaction equation

HRID 2280413 reaction equation
[OH:1][CH2:2][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].[OH-].[Na+].[CH2:15](Br)[CH3:16]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:15]([O:1][CH2:2][C@@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4])[CH3:16]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 14798Sodium HydroxideHCID 545701tert-butyl N-(1-hydroxypropan-2-yl)carbamate

Product 1

HCID 57790784HCID 57790784, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of t-butyl (2-hydroxy-1-methylethyl)carbamate (2.89 g) and tetrabutylammonium hydrogen sulfate (560 mg, 0.1 equiv) in toluene (33 mL) and 50% aqueous sodium hydroxide solution (6.6 mL, 5 equiv) was added ethyl bromide (1.85 mL, 1.5 equiv) at room temperature. The mixture was stirred at room temperature for 4 days. The reaction mixture was partitioned between water and ethyl ether. The organic layer was washed with water and brine, dried over sodium sulfate, and concentrated in vacuo to provide the crude product, which was purified by silica chromatography (9:1 to 75:25 hexanes:ethyl acetate (EtOAc)) to provide the title compound (2.00 g, 60% yield).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl ether
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto provide the crude product, which
  6. customwas purified by silica chromatography (9:1 to 75:25 hexanes:ethyl acetate (EtOAc))

Sources & evidence

ORD record
ord-8a27965c5bef48519684a883c0dd3ac3
Source dataset
uspto-grants-2015_09
Patent number
US09139532B2

Reaction notes

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