Potassium Carbonate → HCID 68616913, compound

HRID 1158477Notes

Reaction equation

HRID 1158477 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].Cl[CH2:14][C:15]1[CH:19]=[C:18]([CH3:20])[O:17][N:16]=1.C([O-])([O-])=O.[K+].[K+].N[C@H:28](C(O)=O)[CH2:29]C1C=C2C(C=CC=C2)=CC=1>CC#N>[CH2:28]([O:6][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([O:1][CH2:14][C:15]2[CH:19]=[C:18]([CH3:20])[O:17][N:16]=2)[CH:3]=1)[CH3:29]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 12575Isovanillic AcidHCID 1859152-NaphthylalanineHCID 27357633-(Chloromethyl)-5-methyl-1,2-oxazole

Product 1

HCID 68616913HCID 68616913, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-hydroxy-4-methoxy-benzoic acid (2.00 g, 10.2 mmol), 3-(chloromethyl)-5-methylisoxazole (1.61 g, 12.2 mmol; commercially available from Maybridge, SPB01262DA), anhydrous K2CO3 (2.11 g, 15.3 mmol) and Nal (0.31 g, 2.04 mmol) in MeCN (35 mL) is refluxed overnight. After cooling to room temperature, the mixture is filtered, the filtrate is diluted with CH2Cl2 and the organics are washed with aqueous 0.5M NaOH, water and brine. Drying over Na2SO4 and evaporation to dryness affords the crude title compound as oil. MS: 292.0 [M+H]+. tR (HPLC, Nucleosil C18HD column, 5-100% CH3CN/H2O/6 min, 100% CH3CN/2 min, CH3CN and H2O containing 0.1% TFA, flow: 1 mL/min): 4.14 min. 1H-NMR (CDCl3): δ 1.39 (t, 3H), 2.45 (s, 3H), 3.93 (s, 3H), 4.35 (q, 2H), 5.20 (s, 2H), 6.15 (s, 1H), 6.15 (dd, 1H), 6.90 (d, 1H), 7.70 (dd, 1H) ppm.

Workup

  1. filtrationthe mixture is filtered
  2. additionthe filtrate is diluted with CH2Cl2
  3. washthe organics are washed with aqueous 0.5M NaOH, water and brine
  4. dry with materialDrying over Na2SO4 and evaporation to dryness

Sources & evidence

ORD record
ord-8b80f95aa2434fa696ce7d93f88f264e
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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