Ethyl bromoacetate → tert-butyl(2S,3S)-2-[(2-ethoxy-2-oxoethyl)amino]-3-methylpentanoate

HRID 1174179Notes

Reaction equation

HRID 1174179 reaction equation
Cl.[C:2]([O:6][C:7](=[O:14])[C@H:8]([C@H:10]([CH2:12][CH3:13])[CH3:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CN(C=O)C>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][NH:9][C@@H:8]([C@@H:10]([CH3:11])[CH2:12][CH3:13])[C:7]([O:6][C:2]([CH3:4])([CH3:5])[CH3:3])=[O:14])[CH3:28]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471Triethylamine2×HCID 11687228tert-Butyl isoleucinate--hydrogen chloride (1/1)

Product 1

HCID 54030946tert-butyl(2S,3S)-2-[(2-ethoxy-2-oxoethyl)amino]-3-methylpentanoateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of L-iso-leucine tert-butyl ester hydrochloride (5 g, 22.34 mmol) in DMF (30 mL) was treated with triethylamine (3.1 mL, 22.34 mmol), stirred for 1 hour at 25° C., filtered to remove solid salts, and the filtrate was treated with triethylamine (9.3 mL, 67.0 mmol) and ethyl bromoacetate (9.9 mL, 67.0 mmol), and the reaction was stirred for 3 hours at 25° C. The reaction mixture was partitioned between ethyl acetate and water, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (5.7 g, 93% yield), which was used without further purification.

Workup

  1. filtrationfiltered
  2. customto remove solid salts
  3. stirringthe reaction was stirred for 3 hours at 25° C
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. washthe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-22877b6024c3469ea062430e59279de5
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

Loading…