Bromoacetyl bromide → HCID 131727451, compound

HRID 494114Notes

Reaction equation

HRID 494114 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][C@@H:8]([CH3:13])[CH2:9][NH:10][CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].C(=O)(O)[O-].[Na+].[Br:20][CH2:21][C:22](Br)=[O:23]>C(OCC)(=O)C>[Br:20][CH2:21][C:22]([CH2:12][CH2:11][NH:10][CH2:9][C@@H:8]([NH:7][C:6](=[O:14])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:13])=[O:23]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 99965190Carbamic acid, [(1S)-2-(ethylamino)-1-methylethyl]-, 1,1-dimethylethyl ester

Product 1

HCID 131727451HCID 131727451, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a cold (0° C.) stirred solution of tert-butyl[(1S)-2-(ethylamino)-1-methylethyl]carbamate (11.0 g, 54.6 mmol) in a mixture of ethyl acetate (107 mL) and saturated aqueous sodium bicarbonate (65 mL), bromoacetyl bromide (12.1 g, 60.0 mmol) was added portionwise under an atmosphere of nitrogen. The mixture was allowed to warm up to room temperature over a period of 3.5 hours. The organic phase was separated, washed successively with saturated aqueous sodium bicarbonate, and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was concentrated as a solution in toluene under vacuum to afford the title compound. ES MS M+1=323, 325.

Workup

  1. additionwas added portionwise under an atmosphere of nitrogen
  2. customThe organic phase was separated
  3. washwashed successively with saturated aqueous sodium bicarbonate, and brine
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. concentrationThe residue was concentrated as a solution in toluene under vacuum

Sources & evidence

ORD record
ord-64dd112132bb4c36a34ed600cbca2250
Source dataset
uspto-grants-2009_05
Patent number
US07538112B2

Reaction notes

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