Triethylamine → HCID 131724210, compound

HRID 479476Notes

Reaction equation

HRID 479476 reaction equation
FC(F)(F)C(O)=O.N[CH:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([NH2:12])=[O:11].[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C:23](Cl)=[O:24])=[CH:19][CH:18]=1.C([N:29](CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[NH2:12][C:10]([CH:9]([C:21]1[CH:22]=[C:17]([CH3:26])[CH:18]=[CH:19][C:20]=1[C:23]([NH2:29])=[O:24])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 18770733HCID 18770733, compound

Product 1

HCID 131724210HCID 131724210, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 22C (489 mg, 3.76 mmol) and p-toluoyl chloride (0.560 mL, 4.14 mmol) in CH2Cl2 (8 mL) at 0° C. was treated with triethylamine (0.520 mL, 3.76 mmol). After 6 hours, the mixture was diluted with ethyl acetate (25 mL) and washed sequentially with 1M HCl (10 mL), saturated aqueous NaHCO3 solution (10 mL), water (15 mL), and brine (10 mL). The organic portion was dried (Na2SO4), filtered, and concentrated to provide an oily residue which was purified by flash chromatography (elution with 50% ethyl acetate/hexanes) to provide 750 mg of the desired product as a sticky white solid.

Workup

  1. washwashed sequentially with 1M HCl (10 mL), saturated aqueous NaHCO3 solution (10 mL), water (15 mL), and brine (10 mL)
  2. dry with materialThe organic portion was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide an oily residue which
  6. customwas purified by flash chromatography (elution with 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-024e5cd24f7340f3bb3f10bc1ace0b5c
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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