Tetramethyltin → N-Isoamyl-N-(6-methyl naphthalene-2-sulfonyl)-D-valine tert-butyl ester

HRID 77323

Reaktionsgleichung

Reaktionsgleichung von HRID 77323
[C:1]([O:5][C:6](=[O:38])[C@@H:7]([CH:35]([CH3:37])[CH3:36])[N:8]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17](OS(C(F)(F)F)(=O)=O)[CH:18]=2)[CH:13]=1)(=[O:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].[Cl-].[Li+].[CH3:41][Sn](C)(C)C>CN(C)C=O.C1(P([Pd](Cl)(Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:38])[C@@H:7]([CH:35]([CH3:36])[CH3:37])[N:8]([CH2:30][CH2:31][CH:32]([CH3:33])[CH3:34])[S:9]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:41])[CH:18]=2)[CH:13]=1)(=[O:10])=[O:11])([CH3:3])([CH3:4])[CH3:2]

Komponenten

6

Edukt 3

HCID 11661TetramethyltinHCID 433294Lithium ChlorideHCID 86653275N-isoamyl-N-(6-trifluoromethanesulfonyloxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester

Produkt 1

HCID 67155284N-Isoamyl-N-(6-methyl naphthalene-2-sulfonyl)-D-valine tert-butyl esterAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178479802HCID 178479802, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of N-isoamyl-N-(6-trifluoromethanesulfonyloxy naphthalene-2-sulfonyl)-D-valine tert-butyl ester (1.1 g, 1.89 mmol) in N,N-dimethylformamide (20 mL) is added lithium chloride (0.40 g, 9.5 mmol), tetramethyl tin (0.525 mL, 3.79 mmol), and bistriphenylphosphino palladium dichloride (0.066 g, 0.095 mmol). The reaction is heated to 80° C. for 16 h. The reaction is allowed to cool to ambient temperature and filtered through Celite. The filtrate is poured over water and extracted three times with dichloromethane. The combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue is purified by column chromatography (4% hexanes-ethyl acetate) to afford the title compound as a white solid (0.41 g, 50% yield).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered through Celite
  3. additionThe filtrate is poured over water
  4. extractionextracted three times with dichloromethane
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by column chromatography (4% hexanes-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-457daebb59124a8c80dea501b501c76d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841291B2

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