Ethyl bromoacetate → HCID 54030181, compound

HRID 243610Notes

Reaction equation

HRID 243610 reaction equation
Cl.[C:2]([O:6][C:7](=[O:13])[C@H:8]([CH:10]([CH3:12])[CH3:11])[NH2:9])([CH3:5])([CH3:4])[CH3:3].C(N(CC)CC)C.Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CN(C)C=O>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][NH:9][C@@H:8]([CH:10]([CH3:11])[CH3:12])[C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:13])[CH3:27]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471Triethylamine2×HCID 12490702tert-butyl (2S)-2-amino-3-methylbutanoate hydrochloride

Product 1

HCID 54030181HCID 54030181, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (L)-valine tert-butyl ester hydrochloride (4.94 g, 23.6 mmol) in N,N-dimethylformamide (55 mL) was added triethylamine (3.28 mL, 1 equivalent), and the mixture was stirred for 1 h. The reaction was filtered to remove solid salts, and the filtrate was treated with triethylamine (9.85 mL, 3 equivalents) and ethyl bromoacetate (7.84 mL, 3 equivalents), and the reaction was stirred for 3 h at 25° C. The reaction was partitioned between ethyl acetate and water, and the organic was washed with brine and dried over MgSO4, filtered and evaporated to give 4.48 g (78%) of the product which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-7d73e3e7ae5e4f26b4b5b9e06f97dedd
Source dataset
uspto-grants-2014_02
Patent number
US08653141B2

Reaction notes

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