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 1460834Notes

Reaction equation

HRID 1460834 reaction equation
[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]

Participants

6

Reactant 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

Product 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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-b625efb7d2a8409a8eaffb5048c2787c
Source dataset
uspto-grants-1991_12
Patent number
US05072006

Reaction notes

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