Boc-Tyr-OMe → (S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester

HRID 879690

Reaktionsgleichung

Reaktionsgleichung von HRID 879690
[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH3:22][C:23]1[C:28]([CH3:29])=[C:27](B(O)O)[CH:26]=[CH:25][N:24]=1.O.CCOC(C)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:27]2[CH:26]=[CH:25][N:24]=[C:23]([CH3:22])[C:28]=2[CH3:29])=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 7019130Boc-Tyr-OMeHCID 22728543Water ethylacetateHCID 58327508(2,3-Dimethylpyridin-4-YL)boronic acid

Produkt 1

HCID 58327260(S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl esterAusbeute 4,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 304 mg of (S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionic acid methyl ester, 314 mg 2,3-dimethylpyridine-4-boronic acid, 374 mg cupric acetate, and 2 grams of powdered 4 Å molecular sieves in 50 mL dry DCM and 0.75 mL TEA was stirred vigorously at rt under an O2 atmosphere for 40 h. The mixture was then poured into water-EtOAc. The organic layer was washed with water and saturated brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (DCM-EtOAc) to provide (S)-2-tert-Butoxycarbonylamino-3-[4-(2,3-dimethyl-pyridin-4-yloxy)-phenyl]-propionic acid methyl ester (18 mg). LCMS (m/z) 401.

Aufarbeitung

  1. washThe organic layer was washed with water and saturated brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (DCM-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-37aeb88988e24c85973cd034d02c9e6a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987295B2

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