Pyridine → (S)-Benzyl 3-methoxy-2-((S)-3-methoxy-2-(2-methyl-N-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)thiazole-5-carboxamido)propanamido)propanoate

HRID 628130Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628130
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][CH2:8][C@H:9]([NH:20][C:21](=[O:35])[C@@H:22]([NH:26][CH2:27][C:28]1[O:29][C:30](=[O:34])[O:31][C:32]=1[CH3:33])[CH2:23][O:24][CH3:25])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:36][C:37]1[S:38][C:39]([C:42](O)=[O:43])=[CH:40][N:41]=1.N1C=CC=CC=1>C(Cl)Cl.Cl>[CH3:6][O:7][CH2:8][C@H:9]([NH:20][C:21](=[O:35])[C@@H:22]([N:26]([CH2:27][C:28]1[O:29][C:30](=[O:34])[O:31][C:32]=1[CH3:33])[C:42]([C:39]1[S:38][C:37]([CH3:36])=[N:41][CH:40]=1)=[O:43])[CH2:23][O:24][CH3:25])[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 988455-Thiazolecarboxylic acid, 2-methyl-HCID 86715351(S)-Benzyl 3-methoxy-2-((S)-3-methoxy-2-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)amino)propanamido)propanoate

Produkt 1

HCID 86715354(S)-Benzyl 3-methoxy-2-((S)-3-methoxy-2-(2-methyl-N-((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)thiazole-5-carboxamido)propanamido)propanoateAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Referring to FIG. 38, phosphorous oxychloride (323 μL, 3.46 mmol) was added dropwise to (S)-benzyl 3-methoxy-2-((S)-3-methoxy-2-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)amino)propanamido)propanoate (1.46 g, 3.46 mmol), 2-methylthiazole-5-carboxylic acid (248 mg, 3.46 mmol) and pyridine (1.07 mL, 10 mmol) in DCM (20 ml) at 0° C. The reaction mixture was stirred at 0° C. for 3 hours, diluted with 1N HCl, and extracted with DCM. The organic layer was separated, dried (Na2SO4) and evaporated. The residue was purified by flash column chromatography to give the product as a white solid (346 mg, 22%).

Aufarbeitung

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c2cca2cd9e9e438f9ecfea57fa0d2c0e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309283B2

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