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N-(Phenylmethyl)-beta-alanine ethyl ester → 3-[Benzyl-(2-chloro-5-nitro-pyrimidin-4-yl)-amino]-propanoic acid ethyl ester

HRID 2111309
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2111309
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].[Cl:16][C:17]1[N:22]=[C:21](Cl)[C:20]([N+:24]([O-:26])=[O:25])=[CH:19][N:18]=1.C(=O)(O)[O-].[K+]>O.C(OCC)C>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][N:7]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:19]1[C:20]([N+:24]([O-:26])=[O:25])=[CH:21][N:22]=[C:17]([Cl:16])[N:18]=1)[CH3:2]
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Komponenten

6

Edukt 3

HCID 90196N-(Phenylmethyl)-beta-alanine ethyl esterHCID 516893Potassium BicarbonateHCID 5212662,4-Dichloro-5-nitropyrimidine

Produkt 1

HCID 581541303-[Benzyl-(2-chloro-5-nitro-pyrimidin-4-yl)-amino]-propanoic acid ethyl esterAusbeute 93,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 1.04 g (0.005 mole) of 3-benzylamino-propanoic acid ethyl ester in 20 mL of water was added dropwise to a solution of 0.97 g (0.005 mole) of 2,4-dichloro-5-nitro-pyrimidine in 20 mL of ethyl ether. At 0 degrees, 1.0 g (0.010 mole) of potassium bicarbonate was added. The mixture was stirred at ambient temperature for 3 hours. The layers were then separated, and the aqueous layer extracted twice with 30 mL of ether. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with hexanes-ethyl acetate (100:0-90:10) gave 1.70 g of 3-[benzyl-(2-chloro-5-nitro-pyrimidin-4-yl)-amino]-propanoic acid ethyl ester (IV-22).

Aufarbeitung

  1. customThe layers were then separated
  2. extractionthe aqueous layer extracted twice with 30 mL of ether
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography
  7. washeluting with hexanes-ethyl acetate (100:0-90:10)

Quellen und Nachweise

ORD-Eintrag
ord-80e22fa1ad6a4cc39aac9fea4840ff29
Quelldatensatz
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07517873B2

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