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 358602

Reaktionsgleichung

Reaktionsgleichung von HRID 358602
[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-244e01cd23f74bf6b94db5e2d81e7baa
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997846

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