Sodium borohydride → HCID 70045181, compound

HRID 1252261Notes

Reaction equation

HRID 1252261 reaction equation
[CH:1]([O:4][C:5](=[O:34])[C:6]1[CH:11]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[Cl:21])[C:10]([C:22](=O)[CH2:23][S:24](=[O:30])(=[O:29])[NH:25][CH:26]([CH3:28])[CH3:27])=[C:9]([CH3:32])[NH:8][C:7]=1[CH3:33])([CH3:3])[CH3:2].[BH4-].[Na+].C(Cl)Cl.C(OCC)(=O)C>C(O)(C)C.COCCOC>[CH:1]([O:4][C:5](=[O:34])[C:6]1[CH:11]([C:12]2[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=2[Cl:21])[C:10](/[CH:22]=[CH:23]/[S:24](=[O:29])(=[O:30])[NH:25][CH:26]([CH3:27])[CH3:28])=[C:9]([CH3:32])[NH:8][C:7]=1[CH3:33])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226138Dichloromethane ethylacetateHCID 70045334HCID 70045334, compound

Product 1

HCID 70045181HCID 70045181, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

Analogously to Example 18, 1.02 g of 4-(2-chloro-5-nitrophenyl)-1,4-dihydro-5-[(isopropylsulfamoyl)acetyl]-2,6-dimethylnicotinic acid isopropyl ester were treated with 0.08 g of sodium borohydride in a mixture of 10 ml of isopropanol and 2 ml of 1,2-dimethoxyethane. After chromatography with methylene chloride/ethyl acetate (4:1) as the elution agent there was obtained 0.70 g of 4-(2-chloro-5-nitrophenyl)-1,4-dihydro-5-[(E)-2-(isopropylsulfamoyl)vinyl]-2,6-dimethylnicotinic acid isopropyl ester in the form of yellow crystals, m.p. 199°-201°.

Sources & evidence

ORD record
ord-6d12d3a2701e418ea3e1dddba04e5552
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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