Triethylamine → HCID 12132988, compound

HRID 1006432Notes

Reaction equation

HRID 1006432 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[CH2:13][C:14](O)=[O:15])=[CH:8][CH:7]=1)=[O:5])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O>C(COC)OC>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH3:24])[CH:18]=2)[CH2:13][CH2:14][OH:15])=[CH:10][CH:11]=1)=[O:5])[CH3:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 12132987HCID 12132987, compound

Product 1

HCID 12132988HCID 12132988, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The resulting 3-(4-diethylcarbamoylphenyl)-3-(3-methoxyphenyl)propionic acid was dissolved in dimethoxyethane (5.6 ml), added with triethylamine (0.12 ml) and isobutyl chloroformate (0.11 ml) under ice cooling and then the mixture was stirred at the same temperature for 30 minutes. Insoluble solids were removed by filtration, and then the filtrate was ice-cooled, added with a solution of sodium borohydride (40.7 mg) dissolved in water (1 ml) and further stirred at the same temperature for 10 minutes. The solvent was evaporated under reduced pressure and added with water (5 ml), and the reaction mixture was extracted twice with dichloromethane (5 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 215 mg of the title compound. Yield: 88% (for the two steps).

Workup

  1. customInsoluble solids were removed by filtration
  2. temperaturecooled
  3. additionadded with a solution of sodium borohydride (40.7 mg)
  4. dissolutiondissolved in water (1 ml)
  5. stirringfurther stirred at the same temperature for 10 minutes
  6. customThe solvent was evaporated under reduced pressure
  7. additionadded with water (5 ml)
  8. extractionthe reaction mixture was extracted twice with dichloromethane (5 ml)
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-402c920cc7b648cca7c81c6269b1e007
Source dataset
uspto-grants-2004_09
Patent number
US06790854B2

Reaction notes

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