Sodium Chloride → HCID 57495615, compound

HRID 1092304Notes

Reaction equation

HRID 1092304 reaction equation
C[C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(Br)[C:3]([OH:5])=[O:4].[CH2:13](N(CC)CC)C.[CH:20]1([NH2:23])[CH2:22][CH2:21]1.[Na+].[Cl-]>CC#N>[CH3:13][O:5][C:3](=[O:4])[CH:2]([NH:23][CH:20]1[CH2:22][CH2:21]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 69828CyclopropylamineHCID 13384353HCID 13384353, compound

Product 1

HCID 57495615HCID 57495615, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

In analogy to a procedure outlined in J. Chem. Soc. Perkin Trans. 1, 22, 1993, 2761-2772, methyl-α-bromophenylacetic acid (2.0 g) was dissolved in CH3CN and cooled to 0° C. by means of an ice bath. To this solution was added triethylamine (1.7 mL) dropwise and the mixture was stirred for 30 minutes. A solution of cyclopropylamine in CH3CN was then added dropwise at 0° C. over 5 minutes and stirring was continued for 2 hours. The mixture was poured into ice/water, saturated with NaCl and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography, eluting with a gradient of ethyl acetate in heptane (0 to 50% ethyl acetate). Fractions containing the product were combined and evaporated to give cyclopropylamino-phenyl-acetic acid methyl ester as a light yellow liquid (1.74 g). MS (ESI): 206.0 (MH+).

Workup

  1. stirringstirring
  2. waitwas continued for 2 hours
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by flash chromatography
  9. washeluting with a gradient of ethyl acetate in heptane (0 to 50% ethyl acetate)
  10. additionFractions containing the product
  11. customevaporated

Sources & evidence

ORD record
ord-6e6f7823317e4cb79fdca60c2c25a649
Source dataset
uspto-grants-2012_03
Patent number
US08129423B2

Reaction notes

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