Bromoacetyl bromide → 2-Bromo-N-((S)-2-hydroxy-2-phenyl-ethyl)-acetamide

HRID 737075

Reaction equation

HRID 737075 reaction equation
[NH2:1][CH2:2][C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[Br:11][CH2:12][C:13](Br)=[O:14]>CCOC(C)=O.C([O-])(O)=O.[Na+]>[Br:11][CH2:12][C:13]([NH:1][CH2:2][C@@H:3]([OH:4])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:14]

Participants

5

Reactant 2

HCID 61147Bromoacetyl bromideHCID 643217(1S)-2-amino-1-phenylethan-1-ol

Product 1

HCID 578495232-Bromo-N-((S)-2-hydroxy-2-phenyl-ethyl)-acetamide

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) biphasic solution of (S)-(+)-2-amino-1-phenylethanol (6.2 g, 45.2 mmol) in EtOAc (450 mL) and saturated aqueous NaHCO3 (125 mL) was added bromoacetyl bromide (4.32 mL, 49.7 mmol) via syringe. The mixture was stirred at 0° C. for 1 h then layers were separated. The aqueous layer was extracted with EtOAc (2×100 mL) then combined organics were dried with Na2SO4, filtered, and concentrated to dryness to afford the desired product as a residue (11.6 g, quant.) that was used in the next transformation: ES MS (+) m/z 258.

Workup

  1. customlayers were separated
  2. extractionThe aqueous layer was extracted with EtOAc (2×100 mL)
  3. dry with materialcombined organics were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0f41999e5516492d8bc0bb872ca32808
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Linked notes

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