Isopropanol → 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(2-methoxy-3-carbonylmethoxy-2-E-propen-1-yl)amino-2H-1-benzopyran

HRID 1460834

Reaktionsgleichung

Reaktionsgleichung von HRID 1460834
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([NH2:15])[C:7]=2[CH:16]=1)#[N:2].ClC/[C:19](/[O:25][CH3:26])=[CH:20]\[C:21](OC)=O.[C:27](=[O:30])([O-])[O-].[K+].[K+].[I-].[Na+].[CH:35]([OH:38])(C)C>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[C@@H:9]([OH:14])[C@H:8]([NH:15]/[CH:21]=[C:20](/[O:30][CH3:27])\[CH2:19][O:25][CH:26]=[C:35]=[O:38])[C:7]=2[CH:16]=1)#[N:2]

Komponenten

6

Edukt 5

HCID 3776IsopropanolHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 6364655Methyl (E)-4-Chloro-3-methoxy-2-butenoateHCID 10943936(3S,4R)-4-amino-3-hydroxy-2,2-dimethyl-chroman-6-carbonitrile

Produkt 1

HCID 867446436-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(2-methoxy-3-carbonylmethoxy-2-E-propen-1-yl)amino-2H-1-benzopyran

Versuchsvorschrift

A mixture of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-amino-2H-1-benzopyran (4.7 g), 4-chloro-3-methoxy-2-E-butenoic acid, methyl ester (3.55 g), potassium carbonate (5.95 g) and sodium iodide (3.2 g) was refluxed for 3 hours in isopropanol. After cooling the mixture was filtered and solvent removed from the filtrate under reduced pressure, to give 1.1 g of 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-hydroxy-4-(2-methoxy-3-carbonylmethoxy-2-E-propen-1-yl)amino-2H-1-benzopyran, a compound of formula (6). The compound was used in the next reaction (Example 3) with no further purification.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered
  3. customsolvent removed from the filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b625efb7d2a8409a8eaffb5048c2787c
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05072006

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