Tyramine → HCID 86612125, compound

HRID 491268Notes

Reaction equation

HRID 491268 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7](O)=[CH:6][CH:5]=1.[H-].[K+].F[C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1.CN(C=[O:31])C>[Cl-].[Na+].O>[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:31][C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 5610TyramineHCID 6228DimethylformamideHCID 82127Potassium hydrideHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 86612125HCID 86612125, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
25 °C

Procedure

Tyramine (700 mg, 5.1 mmol) was added to a magnetically stirred suspension of potassium hydride (35 wt. percent dispersion in oil; 876 mg, 7.64 mmol) in DMF (20 mL) at 25° C. After effervescence stopped, tert-butyl 4-fluorobenzoate (1.0 g, 5.1 mmol) was added. After stirring at 25° C. for 64 hours, the reaction was warmed to 60° C. After 48 h, the reaction was poured into brine and extracted with hexanes (3×25 mL) and ethyl acetate (2×25 mL). Organic layers washed separately with aqueous 2 N NaOH, dried (Na2SO4), then pooled, evaporated and purified by silica gel chromatography (CH2Cl2:MeOH/2:1) to provide 0.98 g of clear oil.

Workup

  1. temperaturethe reaction was warmed to 60° C
  2. waitAfter 48 h
  3. extractionextracted with hexanes (3×25 mL) and ethyl acetate (2×25 mL)
  4. washOrganic layers washed separately with aqueous 2 N NaOH
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. custompurified by silica gel chromatography (CH2Cl2:MeOH/2:1)

Sources & evidence

ORD record
ord-6ff04ba123ff4c089d23aa8a22145eee
Source dataset
uspto-grants-2009_05
Patent number
US07531482B2

Reaction notes

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