tert-Butyl bromoacetate → DI-T-Butyl iminodiacetate

HRID 1397109Notes

Reaction equation

HRID 1397109 reaction equation
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])C(C)(C)C.Br[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]>C(#N)C>[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH2:11][NH:1][CH2:2][C:7]([O:9][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:8]

Participants

4

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 164608L-tert-Leucine

Product 1

HCID 4393691DI-T-Butyl iminodiacetateYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of t-butylglycine (1.40 g, 10.67 mmol) in acetonitrile (20 mL) cooled to 0° C. was added ethyldisopropylamine (1.86 mL, 10.67 mmol) and t-butyl bromoacetate (1.57 mL, 10.67 mmol). The resulting solution was stirred for 24 h at room temperature. The mixture was concentrated to dryness in vacuo, water was added and the solution was extracted with dichloromethane (3×70 mL). The combined organic phases were washed with brine (70 mL), dried over Na2SO4 and concentrated to dryness in vacuo. The crude material was purified by silica gel chromatography (20-80% EtOAc in hexanes) to give the compound 14 (0.88 g, 33.6%). 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 18H), 3.30 (s, 4H).

Workup

  1. concentrationThe mixture was concentrated to dryness in vacuo, water
  2. additionwas added
  3. extractionthe solution was extracted with dichloromethane (3×70 mL)
  4. washThe combined organic phases were washed with brine (70 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness in vacuo
  7. customThe crude material was purified by silica gel chromatography (20-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-198517d0fac94c42853f8dbcc2e369df
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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