Potassium Carbonate → (S)-Benzyl 3-methoxy-2-((S)-3-methoxy-2-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)amino)propanamido)propanoate

HRID 628129Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628129
Cl.[NH2:2][C@@H:3]([CH2:21][O:22][CH3:23])[C:4]([NH:6][C@@H:7]([CH2:18][O:19][CH3:20])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:5].[C:24](=[O:27])([O-:26])[O-:25].[K+].[K+]>CN(C=O)C.O>[CH3:20][O:19][CH2:18][C@H:7]([NH:6][C:4](=[O:5])[C@@H:3]([NH:2][CH2:11][C:12]1[O:27][C:24](=[O:26])[O:25][C:13]=1[CH3:14])[CH2:21][O:22][CH3:23])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 86715352(S)-benzyl 2-((S)-2-amino-3-methoxypropanamido)-3-methoxypropanoate hydrochloride salt

Produkt 1

HCID 86715351(S)-Benzyl 3-methoxy-2-((S)-3-methoxy-2-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)amino)propanamido)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Referring to FIG. 38, 4-(bromomethyl)-5-methyl-1,3-dioxo-2-one (278 mg, 1.44 mmol) was added to (S)-benzyl 2-((S)-2-amino-3-methoxypropanamido)-3-methoxypropanoate hydrochloride salt (1.0 g, 2.88 mmol) and potassium carbonate (400 mg, 2.88 mmol) in DMF (15 mL) at 0° C. The reaction was stirred at 0° for 2.5 hours and then diluted with water and extracted with EtOAc. The extract was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by Biotage flash column chromatography to give product as a yellow oil. MS for C20H26N2O8 m/z: 423 (M+H)+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by Biotage flash column chromatography
  6. customto give product as a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-f5579e8c6f184023bfbc3a1ac1c89d20
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309283B2

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