Potassium Carbonate → HCID 10116680, compound

HRID 2250979Notes

Reaction equation

HRID 2250979 reaction equation
C[O:2][C:3](=[O:16])[CH:4]([OH:15])[CH2:5][C:6]1[CH:11]=[C:10]([Br:12])[C:9]([OH:13])=[C:8]([Br:14])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1>C(#N)C>[Br:14][C:8]1[CH:7]=[C:6]([CH2:5][CH:4]([OH:15])[C:3]([OH:2])=[O:16])[CH:11]=[C:10]([Br:12])[C:9]=1[O:13][CH2:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 703202-BromomethylnaphthaleneHCID 68835944HCID 68835944, compound

Product 1

HCID 10116680HCID 10116680, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of 3-(3,5-dibromo-4-hydroxyphenyl)-2-hydroxypropionic acid methyl ester (0.25 mmol) and potassium carbonate (0.3 mmol) in acetonitrile (5 mL) was stirred for 10 minutes at room temperature under nitrogen. 2-Bromomethylnaphthalene (0.3 mmol) dissolved in acetonitrile (1 mL) was added with a syringe. The reaction mixture was stirred for 15 hours at room temperature under nitrogen. After concentration in vacuo, the light yellow residue was diluted with ethyl acetate (20 mL) and washed with brine (25 mL). The organic phase was dried over magnesium sulphate and concentrated in vacuo. The residue was purified on column (ethyl acetate/n-heptane 1:3). The fractions containing the coupled material were pooled, concentrated and dissolved in methanol (10 mL), and an aqueous solution of lithium hydroxide (10 mL, 1N) was added carefully. The reaction mixture was stirred for 15 hours at room temperature, acidified with hydrochloric acid (2 N) and the volatile solvents removed in vacuo. The formed precipitate was collected, washed with water and purified with HPLC (YMC-Pack, D-C8-5, 250×20 mm, 5 μm, 120A; Mobile phase: 40% acetonitrile and 60% 25 mM ammonium acetate). This gave 11 mg (9%) of 3-[3,5-dibromo-4-(naphthalen-2-ylmethoxy)phenyl]-2-hydroxypropionic acid as a white solid mass. LC/MS (electrospray): m/z 479 (M−1).

Workup

  1. additionwas added with a syringe
  2. stirringThe reaction mixture was stirred for 15 hours at room temperature under nitrogen
  3. concentrationAfter concentration in vacuo
  4. additionthe light yellow residue was diluted with ethyl acetate (20 mL)
  5. washwashed with brine (25 mL)
  6. dry with materialThe organic phase was dried over magnesium sulphate
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified on column (ethyl acetate/n-heptane 1:3)
  9. additionThe fractions containing the coupled material
  10. concentrationconcentrated
  11. dissolutiondissolved in methanol (10 mL)
  12. additionan aqueous solution of lithium hydroxide (10 mL, 1N) was added carefully
  13. stirringThe reaction mixture was stirred for 15 hours at room temperature
  14. customthe volatile solvents removed in vacuo
  15. customThe formed precipitate was collected
  16. washwashed with water
  17. custompurified with HPLC (YMC-Pack, D-C8-5, 250×20 mm, 5 μm, 120A

Sources & evidence

ORD record
ord-3965c29502ef473b98f97148bab324ef
Source dataset
uspto-grants-2008_01
Patent number
US07319096B2

Reaction notes

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