Sodium borohydride → HCID 70416825, compound

HRID 1252259Notes

Reaction equation

HRID 1252259 reaction equation
[CH:1]([O:4][C:5](=[O:32])[C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10]([C:21](=O)[CH2:22][S:23](=[O:28])(=[O:27])[NH:24][CH2:25][CH3:26])=[C:9]([CH3:30])[NH:8][C:7]=1[CH3:31])([CH3:3])[CH3:2].[BH4-].[Na+].C(Cl)Cl.C(OCC)(=O)C>C(O)(C)C.CN(C)C=O>[CH:1]([O:4][C:5](=[O:32])[C:6]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:10](/[CH:21]=[CH:22]/[S:23](=[O:27])(=[O:28])[NH:24][CH2:25][CH3:26])=[C:9]([CH3:30])[NH:8][C:7]=1[CH3:31])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226138Dichloromethane ethylacetateHCID 70415797HCID 70415797, compound

Product 1

HCID 70416825HCID 70416825, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

Analogously to Example 18, 1.86 g of 5-[(ethylsulfamoyl)acetyl]-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid isopropyl ester were treated with 0.16 g of sodium borohydride in a mixture of 20 ml of isopropanol and 4 ml of dimethylformamide. After chromatography with methylene chloride/ethyl acetate (4:1) as the elution agent there were obtained 1.5 g of 5-[(E)-2-(ethylsulfamoyl)vinyl]-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid isopropyl ester in the form of yellow crystals, m.p. 187°-189°. Recrystallization from methylene chloride/ether did not increase the melting point.

Sources & evidence

ORD record
ord-65e45af608cf4406bdeb4f6f1c0d0e2a
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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