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Potassium Carbonate → methyl (R)-2-tert-butoxycarbonylamino-3-(3'-formylbiphenyl-4-yl)propionate

HRID 271857
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 271857
[C:1](=[O:4])([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([NH:14][C@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24](OS(C(F)(F)F)(=O)=O)=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]>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.[Pd]>[C:7]([O:11][C:12]([NH:14][C@H:15]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH:1]=[O:4])[CH:22]=2)=[CH:23][CH:22]=1)[C:16]([O:18][CH3:19])=[O:17])=[O:13])([CH3:10])([CH3:9])[CH3:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 53983472(R)-methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(((trifluoromethyl)sulfonyl)oxy)phenyl)propanoate

Produkt 1

HCID 86601623methyl (R)-2-tert-butoxycarbonylamino-3-(3'-formylbiphenyl-4-yl)propionateAusbeute 35 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178527696HCID 178527696, VerbindungKatalysator
HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

100 ml (201 mmol) of an aqueous 2M potassium carbonate solution and 4.4 g (3.80 mmol) of tetrakis palladium are introduced into a solution containing 33 g (77.3 mmol) of methyl (R)-2-tert-butoxycarbonylamino-3-(4-trifluoromethanesulfonyloxyphenyl)propionate, and 15 g (100 mmol) of 3-boronic acid-benzaldehyde (Example 28b) in 300 ml of ethylene glycol dimethyl ether. The reaction medium is heated at 85° C. for 20 h and, after a return to ambient temperature, extracted with ethyl acetate. The organic phase is washed with water and then a saturated sodium chloride solution, dried over magnesium sulfate, and concentrated. The residue obtained is purified by chromatography on a column of silica and eluted with a 7/3 heptane/ethyl acetate mixture. 10.2 g of coupled product are obtained with a 35% yield.

Aufarbeitung

  1. extractionafter a return to ambient temperature, extracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materiala saturated sodium chloride solution, dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a 7/3 heptane/ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-043578fe9d47433a91e8bf99c4dc3215
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07452878B2

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