Ethyl Acetate → methyl N-[(4'-nitro-1,1'-biphenyl-4-yl)sulfonyl]-L-valinate

HRID 29281

Reaktionsgleichung

Reaktionsgleichung von HRID 29281
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N+:20]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)([O-:22])=[O:21].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N+:20]([C:23]1[CH:28]=[CH:27][C:26]([C:2]2[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])(=[O:10])=[O:9])=[CH:4][CH:3]=2)=[CH:25][CH:24]=1)([O-:22])=[O:21]

Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 27735524-Nitrophenylboronic acidHCID 47337186methyl N-[(4-bromophenyl)sulfonyl]-L-valinate

Produkt 1

HCID 10069077methyl N-[(4'-nitro-1,1'-biphenyl-4-yl)sulfonyl]-L-valinateAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A mixture of 0.175 g (0.5 mmol) of methyl N-[(4-bromophenyl)sulfonyl]-L-valinate, 0.25 g (1.5 mmol) of 4-nitrophenylboronic acid, 0.087 g of tetrakis(triphenylphosphine)palladium and 8 mL of saturated sodium bicarbonate in 8 mL of ethylene glycol dimethyl ether were refluxed for 2 h, then cooled to room temperature. To the reaction was added 50 mL of ethyl acetate and 40 mL of water. The water layer was extracted with ethyl acetate. The combined ethyl acetate layers was dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography, eluting with hexane:ethyl acetate (2:1) to provide 0.159 g of methyl N-[(4′-nitro-1,1′-biphenyl-4-yl)sulfonyl]-L-valinate as a yellow solid. Yield 81%. m.p. 144-146° C.; MS: 391.0(M−H)−.

Aufarbeitung

  1. temperaturewere refluxed for 2 h
  2. extractionThe water layer was extracted with ethyl acetate
  3. dry with materialThe combined ethyl acetate layers was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography
  7. washeluting with hexane:ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-0a555bc7f2294e2684f21f1665cd84dc
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420001B2

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