4-Methylmorpholine → 4-Fluorocinnamoyl-glycine methyl ester

HRID 248814

Reaktionsgleichung

Reaktionsgleichung von HRID 248814
[CH3:1][O:2][C:3](=[O:16])[CH2:4][NH:5][C:6](=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl.COC(=O)CN.CN1CCOCC1.[F:31]C1C=CC(C=CC(O)=O)=CC=1.C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>O1CCCC1>[CH3:1][O:2][C:3](=[O:16])[CH2:4][NH:5][C:6](=[O:15])[CH:7]=[CH:8][C:9]1[CH:10]=[CH:11][C:12]([F:31])=[CH:13][CH:14]=1

Komponenten

8

Edukt 6

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 980703-(4-Fluorophenyl)-2-propenoic acidHCID 122755Glycine methyl ester hydrochlorideHCID 582979Glycine,n-(1-oxo-3-phenyl-2-propen-1-yl)-, methyl ester

Produkt 1

HCID 536568534-Fluorocinnamoyl-glycine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Following the general procedure described in example 1, step 2, for cinnamoyl-glycine methyl ester, glycine methyl ester hydrochloride (7.5 g) was suspended in tetrahydrofuran, cooled to 0° C., treated with N-methylmorpholine (8.4 ml, 1 equivalent), followed immediately by a precooled solution of 4-fluorocinnamic acid (10.0 g) in tetrahydrofuran, which had been pre-activated by treatment with dicyclohexylcarbodiimide (12.4 g, 1 equivalent) and 1-hydroxybenzotriazole (9.2 g). After work-up, 4-fluorocinnamoyl-glycine methyl ester was obtained as a white solid which was used for the next step without further purification.

Quellen und Nachweise

ORD-Eintrag
ord-c99bff5c88ba41f8bd02708dafbd874d
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05212158

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