Diisopropylethylamine → (2R,4S)-4-((tert-Butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl 2-fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzenesulfonate

HRID 628146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 628146
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[NH:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[S:14](Cl)(=[O:16])=[O:15].[OH:18][CH2:19][C@:20]([OH:37])([CH3:36])[C:21](=[O:35])[C@@H:22]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:23][CH:24]([CH3:26])[CH3:25].CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[NH:9][CH2:10][C:11]#[CH:12])=[CH:4][C:3]=1[S:14]([O:18][CH2:19][C@:20]([OH:37])([CH3:36])[C:21](=[O:35])[C@@H:22]([NH:27][C:28]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:34])[CH2:23][CH:24]([CH3:26])[CH3:25])(=[O:15])=[O:16]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 867153592-Fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzene-1-sulfonyl chlorideHCID 86715361tert-butyl ((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)carbamate

Produkt 1

HCID 86715360(2R,4S)-4-((tert-Butoxycarbonyl)amino)-2-hydroxy-2,6-dimethyl-3-oxoheptyl 2-fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzenesulfonateAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-Fluoro-5-(prop-2-yn-1-ylcarbamoyl)benzene-1-sulfonyl chloride (3, 2.52 g, 9.14 mmol) was added dropwise to tert-butyl ((2R,4S)-1,2-dihydroxy-2,6-dimethyl-3-oxoheptan-4-yl)carbamate (2.65 g, 9.14 mmol), DIEA (1.91 mL, 10 mmol) and DMAP (0.1 g, 0.914 mmol) in DCM (30 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The reaction was washed with 2N HCl and brine, dried (MgSO4) and evaporated. The residue was purified by Biotage flash column chromatography (30% EtOAc/Hep) to give product as an oil (3.62 g, 75%).

Aufarbeitung

  1. washThe reaction was washed with 2N HCl and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by Biotage flash column chromatography (30% EtOAc/Hep)

Quellen und Nachweise

ORD-Eintrag
ord-02b939fb576441cc80a66a0b0e56906e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309283B2

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