1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [2-(3-Fluoro-phenyl)-ethoxy]-acetic acid methyl ester

HRID 2100503Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2100503
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][O:10][CH2:11][C:12]([OH:14])=[O:13])[CH:5]=[CH:6][CH:7]=1.[CH3:15]CN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CO.C(Cl)Cl>[CH3:15][O:13][C:12](=[O:14])[CH2:11][O:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Komponenten

7

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 24769444953786-95-3

Produkt 1

HCID 67099252[2-(3-Fluoro-phenyl)-ethoxy]-acetic acid methyl esterAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of [2-(3-fluoro-phenyl)-ethoxy]-acetic acid (1.20 g, 6.05 mmol), EDCI (1.28 g, 6.66 mmol), HOBt (0.90 g, 6.66 mmol) and DIPEA (1.56 ml, 9.08 mmol) in methanol (4 ml) was stirred at 0° C. for 2 hours. The reaction mixture was brought to dryness, dissolved in CH2Cl2 and washed twice with 1M NaOH and brine. The organic layers were dried over MgSO4, filtrated, the solvent was removed under reduced pressure and the residue was purified by column chromatography (silica gel, EtOAc/heptane, 1/4) to yield [2-(3-fluoro-phenyl)-ethoxy]-acetic acid methyl ester (1.20 g, 5.6 mmol; 93%) as colorless liquid. MS (m/e): 213.2 [M+H]+.

Aufarbeitung

  1. washwashed twice with 1M NaOH and brine
  2. dry with materialThe organic layers were dried over MgSO4
  3. filtrationfiltrated
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (silica gel, EtOAc/heptane, 1/4)

Quellen und Nachweise

ORD-Eintrag
ord-af11832e814f4a2cab5def56bac7df07
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572801B2

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