Sodium Methoxide → 7-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester

HRID 706175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706175
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17][N:18]([CH2:29][C:30]([O:32][CH3:33])=[O:31])S(C1C=CC(C)=CC=1)(=O)=O.C[O-].[Na+]>CO>[CH3:33][O:32][C:30]([C:29]1[N:18]=[CH:17][C:5]2[C:4]([C:3]=1[OH:2])=[CH:9][CH:8]=[C:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH:6]=2)=[O:31]

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 671108664-Benzyl-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester

Produkt 1

HCID 671101307-Benzyl-4-hydroxy-isoquinoline-3-carboxylic acid methyl esterAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of crude 4-benzyl-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid methyl ester (1.54 g) in methanol (1.75 mL) was added a solution of NaOMe (30 wt %) in methanol (1.75 mL) with stirring. After stirring for 5 h at ambient temperature the mixture was concentrated in vacuo and water (20 mL) was added. The pH of the mixture was adjusted to 7 to 8 by addition of 6N hydrochloric acid before the mixture was extracted with ethyl acetate (2×25 mL). The combined organic phases were then dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using hexanes:ethyl acetate=7:3 as the eluent to give the title compound as an off-white solid (451 mg); MS-(+)-ion: M+1=294.0.

Aufarbeitung

  1. stirringAfter stirring for 5 h at ambient temperature the mixture
  2. concentrationwas concentrated in vacuo and water (20 mL)
  3. additionwas added
  4. additionThe pH of the mixture was adjusted to 7 to 8 by addition of 6N hydrochloric acid before the mixture
  5. extractionwas extracted with ethyl acetate (2×25 mL)
  6. dry with materialThe combined organic phases were then dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-25240450dca5467eba125242ec367096
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174976B2

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