Sodium borohydride → HCID 86742153, compound

HRID 1252263Notes

Reaction equation

HRID 1252263 reaction equation
[C:1]1([C@H:7]([O:9][C:10](=[O:38])[C:11]2[C@@H:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[C:15]([C:26](=O)[CH2:27][S:28](=[O:34])(=[O:33])[NH:29][CH:30]([CH3:32])[CH3:31])=[C:14]([CH3:36])[NH:13][C:12]=2[CH3:37])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+]>C(O)(C)C.CN(C)C=O>[C:1]1([C@H:7]([O:9][C:10](=[O:38])[C:11]2[C@@H:16]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[C:15](/[CH:26]=[CH:27]/[S:28](=[O:34])(=[O:33])[NH:29][CH:30]([CH3:32])[CH3:31])=[C:14]([CH3:36])[NH:13][C:12]=2[CH3:37])[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 86742154HCID 86742154, compound

Product 1

HCID 86742153HCID 86742153, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

Analogously to Example 18, 1.08 g of (S)-1,4-dihydro-5-[(isopropylsulfamoyl)acetyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid (R)-1-phenylethyl ester were treated with 0.08 g of sodium borohydride in a mixture of 10 ml of isopropanol and 2 ml of dimethylformamide. The product was chromatographed with methylene chloride/ethyl acetate (4:1) as the elution agent and then recrystallized from ethanol. There was obtained 0.82 g of (S)-1,4-dihydro-5-[(E)-2-(isopropylsulfamoyl)vinyl]-2,6-dimethyl-4-(3-nitrophenyl)nicotinic acid (R)-1-phenylethyl ester in the form of yellow crystals, m.p. 198°-201°, specific rotation: [α]54620 =-290° (c=1.0% w/v, chloroform).

Workup

  1. customThe product was chromatographed with methylene chloride/ethyl acetate (4:1) as the elution agent
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-07e26701000247bca9af1a38bd9d9a0d
Source dataset
uspto-grants-1988_05
Patent number
US04742069

Reaction notes

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