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4-Methylmorpholine → Methyl 3-(4-chlorophenyl)-2-formamidopropanoate

HRID 1392728
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1392728
[ClH:1].[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH3:14])[NH:6][C:7]1C=CC(Cl)=CC=1.Cl.CN(C)CCCN=C=NCC.[OH2:28].ON1[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2N=N1.CN1CCOCC1>C(Cl)Cl.C(O)=O>[Cl:1][C:33]1[CH:38]=[CH:37][C:36]([CH2:14][CH:5]([NH:6][CH:7]=[O:28])[C:4]([O:3][CH3:2])=[O:15])=[CH:35][CH:34]=1
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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 14318072Methyl 3-(4-chlorophenyl)-2-formamidopropanoateAusbeute 62,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittel2×HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(±)-(4-Chlorophenyl)alanine methyl ester hydrochloride (2.00 g) was suspended in methylene chloride (20 ml), and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (1.60 g), 1-hydroxybenzo-triazole 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 methylene chloride. After an ogranic 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 (methylene chloride:methanol=40:1) to obtain the title compound (1.21 g).

Aufarbeitung

  1. stirringto stir the mixture for 15 minutes
  2. washAfter an ogranic 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 (methylene chloride:methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-6f9a1867d1e54b28ad7763b8635f9791
Quelldatensatz
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07342014B2

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