Triethylamine → HCID 22375580, compound

HRID 1600542Notes

Reaction equation

HRID 1600542 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[Br:17][CH:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19](Cl)=[O:20].C(=O)([O-])O.[Na+]>C(#N)C>[Br:17][CH:18]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:19]([NH:8][C:9]([CH3:16])([CH3:15])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 70683Alanine, 2-methyl-, ethyl esterHCID 516892Sodium BicarbonateHCID 598182Bromophenylacetyl chloride

Product 1

HCID 22375580HCID 22375580, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

Triethylamine (11 g) was added suspension of ethyl aminoisobutyrate (7.5 g) in acetonitrile (80 mL) cooled to 0° C., and to the mixture was slowly added dropwise a solution of α-bromophenylacetyl chloride (11 g) in acetonitrile (20 mL). After the addition was completed, the solution was warmed to room temperature, and stirred overnight. The reaction solution was poured into a sodium hydrogencarbonate aqueous solution and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure, and then the resulting crude product was washed with diisopropyl ether to give 6.4 g of ethyl 2-(α-bromophenylacetylamino)isobutyrate.

Workup

  1. additionAfter the addition
  2. temperaturethe solution was warmed to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washthe resulting crude product was washed with diisopropyl ether

Sources & evidence

ORD record
ord-8659b29ce40e4771a113d05802067cff
Source dataset
uspto-grants-1999_11
Patent number
US05977027

Reaction notes

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