4-Methylmorpholine → (+/-)-N-Formyl-(4-chlorophenyl)alanine methyl ester

HRID 546495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 546495
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH3:14])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CC[O:43][CH2:42]C1>ClCCl.C(O)=O>[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH3:14])[N:6]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH:42]=[O:43]

Komponenten

7

Edukt 4

HCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67056399(+/-)-(4-Chlorophenyl)alanine methyl ester hydrochloride

Produkt 1

HCID 18442857(+/-)-N-Formyl-(4-chlorophenyl)alanine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(±)-(4-Chlorophenyl)alanine methyl ester hydrochloride (2.00 g) was suspended in dichloromethane (20 ml), and 3-(3-dimethylaminopropyl)-1-ethylcarbodiimide hydrochloride (1.60 g), 1-hydroxybenzotriazole monohydrate (1.23 g), N-methylmorpholine (1.90 ml) and formic acid (0.30 ml) were added to stir the mixture for 15 minutes. After a process in which formic acid (0.30 ml) was additionally added to stir the mixture for 15 minutes was repeated 3 times, the reaction mixture was diluted with dichloromethane. After an organic layer was washed with water and then dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=40:1) to obtain the title compound (1.21 g) as a yellow oil.

Aufarbeitung

  1. stirringto stir the mixture for 15 minutes
  2. washAfter an organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-dc5467e7a6c7489b9164ad1deb780bba
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935824B2

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