Potassium Carbonate → (S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

HRID 58364

Reaktionsgleichung

Reaktionsgleichung von HRID 58364
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][CH2:30][CH:31]=[CH2:32]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:21])[C@@H:4]([NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:32][CH2:31][CH:30]=[CH2:29])=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 21241Homoallyl bromideHCID 7019130Boc-Tyr-OMe

Produkt 1

HCID 66846982(S)-3-(4-But-3-enyloxy-phenyl)-2-tert-butoxycarbonylamino-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

N-BOC-tyrosine methyl ester (10.0 g, 33.9 mmol) was dissolved in DMF (40 mL) and potassium carbonate (5.62 g, 40.7 mmol) and 4-bromo-1-butene (4.13 mL, 40.7 mmol) were added. The mixture was stirred at rt for 18 h before being diluted with EtOAc (120 mL) and partitioned with 1M hydrochloric acid. The organic phase was washed with hydrochloric acid and then with brine before being dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether to yield a white solid, 3.20 g, 27%. Rf=0.82 (1/2 EtOAc/(50/70) petroleum ether).

Aufarbeitung

  1. custompartitioned with 1M hydrochloric acid
  2. washThe organic phase was washed with hydrochloric acid
  3. dry with materialwith brine before being dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography on silica using a gradient of EtOAc and (50/70) petroleum ether
  7. customto yield a white solid, 3.20 g, 27%

Quellen und Nachweise

ORD-Eintrag
ord-53224240deee4475a371d6a18ca920cc
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434762B2

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