Hydrochloric Acid → 4-{[(2-Fluoro-4-hydroxy-6-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl ester

HRID 2261837Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2261837
[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([O:20][Si](C(C)C)(C(C)C)C(C)C)=[CH:15][C:14]=2[F:31])[CH3:12])=[CH:6][C:5]=1[CH3:32].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1>[CH3:1][O:2][C:3](=[O:33])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([OH:20])=[CH:15][C:14]=2[F:31])[CH3:12])=[CH:6][C:5]=1[CH3:32]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2724141Tetrabutylammonium FluorideHCID 574433494-{[(2-Fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl ester

Produkt 1

HCID 675280644-{[(2-Fluoro-4-hydroxy-6-methyl-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl esterAusbeute 76,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of 4-{[(2-fluoro-6-methyl-4-triisopropylsilanyloxy-phenyl)-methyl-amino]-methyl}-2-methyl-benzoic acid methyl ester (457 mg, 0.965 mmol) and tetrabutylammonium fluoride (2.0 mL of 1M in THF, 2.0 mmol) in THF (10 mL) is stirred at 0° C. for 20 minutes and then 2.0 mL of 1M HCl is added and the mixture is concentrated. The residue is portioned between ethyl acetate and brine. The layers are separated and the brine layer is extracted with ethyl acetate. The combined ethyl acetate layers are dried (MgSO4) and concentrated. The residue is purified on 40 g silica with ethyl acetate in heptane gradient (10% to 70%) to provide 233 mg (76%) of the titled compound as a glass. LC-ES/MS m/e 318.2 (M+1).

Aufarbeitung

  1. concentrationthe mixture is concentrated
  2. customThe layers are separated
  3. extractionthe brine layer is extracted with ethyl acetate
  4. dry with materialThe combined ethyl acetate layers are dried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is purified on 40 g silica with ethyl acetate in heptane gradient (10% to 70%)

Quellen und Nachweise

ORD-Eintrag
ord-f2758d59b18d41259792b9ea7dad92b1
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846960B2

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