Methyl bromoacetate → HCID 12012099, compound

HRID 841136Notes

Reaction equation

HRID 841136 reaction equation
[CH3:1][C@H:2]([NH2:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>C(#N)C.C(OCC)(=O)C>[C:3]1([C@@H:2]([NH:9][CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH3:1])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 60984Methyl bromoacetateHCID 758181-Phenethylamine, (-)-HCID 81531Diisopropylethylamine

Product 1

HCID 12012099HCID 12012099, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-α-methylbenzylamine (3.87 mL, 0.03 mol) in acetonitrile (50 mL) was added diisopropylethylamine (5.23 mL, 0.03 mol), followed by methyl bromoacetate (2.84 mL, 0.03 mol). The reaction was stirred under nitrogen, at room temperature, overnight. The solution was concentrated and the residue partitioned between ethyl acetate and saturated NaHCO3. The aqueous layer was separated, and the product extracted three times with ethyl acetate. The ethyl acetate solutions were combined, washed three times with brine, dried over MgSO4, and concentrated to give a light yellow liquid. Chromatography was carried out on silica gel, using ethyl acetate as eluent, to give a colorless liquid; 4.97 g (86% yield). MS-APCI: M+1=194.2.

Workup

  1. concentrationThe solution was concentrated
  2. customthe residue partitioned between ethyl acetate and saturated NaHCO3
  3. customThe aqueous layer was separated
  4. extractionthe product extracted three times with ethyl acetate
  5. washwashed three times with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give a light yellow liquid
  9. customto give a colorless liquid

Sources & evidence

ORD record
ord-ec78e352c624483a8dbe9f8f33f90eef
Source dataset
uspto-grants-2002_04
Patent number
US06369034B1

Reaction notes

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