Triethylamine → HCID 58310923, compound

HRID 1189571Notes

Reaction equation

HRID 1189571 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(N(CC)CC)C.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([CH2:32][C:33](=O)[CH3:34])[C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=O)=[CH:19][CH:18]=1>C(O)C.C(Cl)Cl>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:32]=[C:33]([CH3:34])[N:2]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:24]=2[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 58310954HCID 58310954, compound

Product 1

HCID 58310923HCID 58310923, compoundYield 42.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

Ethyl 2-aminoacetate hydrochloride (0.775 g, 5.55 mmol) was diluted with ethanol (5 ml) then triethylamine was added (1.160 ml, 8.32 mmol), followed by 2-(4-fluorophenyl)-1-phenylpentane-1,4-dione (1.5 g, 5.55 mmol), added as a solution in DCM. The reaction was heated at 100° C. overnight, after which TLC showed a new spot (less polar, Rf˜0.9 in 20% EtOAc/hexanes). The reaction was diluted with 10 mL DCM and washed with water (10 mL) and the aqueous layer was back-extracted with DCM (10 mL×2). The organics were combined, dried, filtered, and concentrated under vacuum to yield a crude orange oil. This oil was loaded onto a SiO2 column and purified using a 0-20% gradient of EtOAc in hexanes, affording the desired product ethyl 2-(3-(4-fluorophenyl)-5-methyl-2-phenyl-1H-pyrrol-1-yl)acetate (0.804 g, 2.383 mmol, 42.9% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.36-7.34 (m, 3H), 7.26-7.22 (m, 2H), 7.11-7.07 (m, 2H), 6.85-6.81 (m, 2H), 6.20 (b, 1H), 4.42 (s, 2H), 4.21 (q, 2H), 2.26 (s, 3H), 1.25 (t, 3H).

Workup

  1. washwashed with water (10 mL)
  2. extractionthe aqueous layer was back-extracted with DCM (10 mL×2)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customto yield a crude orange oil
  7. custompurified

Sources & evidence

ORD record
ord-d36c162679684541b408de48b1863db8
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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