Dimethylformamide → Boc-L-Homoser-Obzl

HRID 79911Notes

Reaction equation

HRID 79911 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH2:10][CH2:11][OH:12])=[O:7])([CH3:4])[CH3:3].C(=O)(O)[O-].[K+].CN(C)C=O.[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(OCC)(=O)C>[C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH2:11][OH:12])[C:13]([O:15][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:14])=[O:7])([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 516893Potassium BicarbonateHCID 13066457(2S)-2-(((tert-butoxy)carbonyl)amino)-4-hydroxybutanoic acid

Product 1

HCID 13970788Boc-L-Homoser-Obzl

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-t-Boc-L-homoserine (5.14 g, 23.45 mmol) and potassium bicarbonate (2.46 g, 24.6 mmol) was weighed out in a round bottom flask and to it was added anhydrous N,N-dimethylformamide (100 mL) and benzyl bromide (4.2 g, 24.6 mmol). The mixture was stirred at room temperature for 18 hours. The crude mixture was then diluted with ethyl acetate and washed, respectively, with brine, saturated NaHCO3 and brine, and dried over Na2SO4. The organic layer was then concentrated down on rotovap and purified on normal phase column chromatography. Yield=7.27 g (100%).

Workup

  1. washwashed
  2. dry with materialrespectively, with brine, saturated NaHCO3 and brine, and dried over Na2SO4
  3. concentrationThe organic layer was then concentrated down on rotovap
  4. custompurified on normal phase column chromatography

Sources & evidence

ORD record
ord-a5ed0ce01bdf4ee2b455f457585d0cb1
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

Loading…