Sodium Carbonate → (IR)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-phenylethylamide

HRID 478160Notes

Reaction equation

HRID 478160 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C@@H:7]([NH2:10])[CH2:8][OH:9])=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[Br:17][C:18]1([C:21](Cl)=[O:22])[CH2:20][CH2:19]1.[OH-].[Na+]>C(Cl)Cl.O>[OH:9][CH2:8][C@H:7]([NH:10][C:21]([C:18]1([Br:17])[CH2:20][CH2:19]1)=[O:22])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 2724025(R)-beta-aminophenethyl alcoholHCID 109102061-Bromocyclopropane-carboxylic acid chloride

Product 1

HCID 21350875(IR)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-phenylethylamideYield 71.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

739 mg of D-(−)-α-phenylglycinol is dissolved in 27 ml of methylene chloride, and 678 mg of sodium carbonate is added to 11 ml of water and 1.09 g of acid chloride 107 at room temperature. It is stirred overnight and then mixed with methanolic sodium hydroxide solution, the organic phase is separated, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with ethyl acetate/hexane, whereby 1.09 g of (1R)-1-bromocyclopropanecarboxylic acid-2-hydroxy-1-phenylethylamide 110 is isolated as a colorless oil.

Workup

  1. customthe organic phase is separated
  2. customdried on sodium sulfate
  3. concentrationconcentrated by evaporation
  4. customThe residue is chromatographed on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-e6928768b20a42ef83d70c01fd8ee553
Source dataset
uspto-grants-2003_11
Patent number
US06642218B2

Reaction notes

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