Dimethylformamide → 3-[(2S,3S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-fluorophenyl)-1-oxobutanyl]thiazolidine

HRID 970207Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970207
[N:1]([C@@H:4]([C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH3:9])[C:5]([OH:7])=O)=[N+]=[N-].Cl.CN(C)CCCN=C=NCC.[OH:29][C:30]1[C:38]2N=NNC=2C=C[CH:31]=1.[S:39]1[CH2:43][CH2:42][NH:41][CH2:40]1.[CH3:44]CN(C(C)C)C(C)C.CN(C)[CH:55]=[O:56]>C(OCC)(=O)C>[C:30]([O:29][C:55]([NH:1][C@@H:4]([C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[CH3:9])[C:5]([N:41]1[CH2:42][CH2:43][S:39][CH2:40]1)=[O:7])=[O:56])([CH3:31])([CH3:38])[CH3:44]

Komponenten

8

Edukt 6

HCID 6228DimethylformamideHCID 10444ThiazolidineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86605120(2S,3S)-2-Azido-3-(4-fluorophenyl)butanoic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 694229793-[(2S,3S)-2-[(tert-Butoxycarbonyl)amino]-3-(4-fluorophenyl)-1-oxobutanyl]thiazolidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of the product from Step D (0.19 g, 0.65 mmol) in anhydrous dimethylformamide (DMF, 2 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 0.19 g, 0.99 mmol), hydroxybenzotriazole (HOBT, 0.13 g, 0.96 mmol), thiazolidine (0.26 mL, 3.3 mmol) and N,N′-diisopropylethylamine (0.33 mL, 1.9 mmol). After stirring at room temperature for 12 h, the reaction was diluted with ethyl acetate. The organic phase was washed sequentially with brine, 1N hydrochloric acid and 1N aqueous sodium hydroxide solution, dried over sodium sulfate, and evaporated in vacuo to yield the crude coupled product, which was used directly in the next step.

Aufarbeitung

  1. washThe organic phase was washed sequentially with brine, 1N hydrochloric acid and 1N aqueous sodium hydroxide solution
  2. dry with materialdried over sodium sulfate
  3. customevaporated in vacuo
  4. customto yield the crude

Quellen und Nachweise

ORD-Eintrag
ord-9e57c806683349efb7c4a76b49115741
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07309714B2

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