Sodium borohydride → HCID 70416706, compound

HRID 1252260Notes

Reaction equation

HRID 1252260 reaction equation
[F:1][C:2]([F:35])([F:34])[CH2:3][O:4][C:5](=[O:33])[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:29])(=[O:28])[NH:24][CH:25]([CH3:27])[CH3:26])=[C:9]([CH3:31])[NH:8][C:7]=1[CH3:32].[BH4-].[Na+].C(Cl)Cl.C(OCC)(=O)C>C(O)(C)C>[F:34][C:2]([F:1])([F:35])[CH2:3][O:4][C:5](=[O:33])[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:28])(=[O:29])[NH:24][CH:25]([CH3:27])[CH3:26])=[C:9]([CH3:31])[NH:8][C:7]=1[CH3:32]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226138Dichloromethane ethylacetateHCID 70416973HCID 70416973, compound

Product 1

HCID 70416706HCID 70416706, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Analogously to Example 18, a solution of 1.56 g of 1,4-dihydro-5-[(isopropylsulfamoyl)acetyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2,2,2-trifluoroethyl ester in 15 ml of isopropanol was treated with 0.12 g (3 mmol) of sodium borohydride. After chromatography with methylene chloride/ethyl acetate (4:1) as the elution agent there were obtained 1.25 g of 1,4-dihydro-5-[(E)-2-(isopropylsulfamoyl)vinyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid 2,2,2-trifluoroethyl ester in the form of yellow crystals, m.p. 180°-182°. Recrystallization from isopropanol did not increase the melting point.

Sources & evidence

ORD record
ord-ea6416f1defd4c32b3c5d38916e1259c
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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