Methanol → HCID 23499504, compound

HRID 1836333Notes

Reaction equation

HRID 1836333 reaction equation
[CH2:1]([S:8]([NH:11][NH:12][C:13]1[C:14](=[O:27])[N:15]([CH2:20][CH2:21][C:22](OCC)=[O:23])[C:16]([CH3:19])=[CH:17][N:18]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[BH4-].[Na+]>O1CCCC1.O.ClCCl>[CH2:1]([S:8]([NH:11][NH:12][C:13]1[C:14](=[O:27])[N:15]([CH2:20][CH2:21][CH2:22][OH:23])[C:16]([CH3:19])=[CH:17][N:18]=1)(=[O:9])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 23499489HCID 23499489, compound

Product 1

HCID 23499504HCID 23499504, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-benzylsulfonylhydrazino)-1-[(2-ethoxycarbonyl)ethyl]-6-methylpyrazinone, the product of Example 30 (0.398 g, 1.01 mmol), in tetrahydrofuran (10 mL) containing 5% methanol, is added sodium borohydride (0.229 g, 6.07 mmol) at room temperature. The reaction mixture is stirred for 5 hours. Water (2 mL) is then added and the mixture is fractionated between dichloromethane and water. The organic phase is dried over anhydrous sodium sulfate and is concentrated under reduced pressure. The crude residue is purified using silica gel column chromatography with ethyl acetate/n-hexane as eluent to afford the title compound.

Workup

  1. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  2. concentrationis concentrated under reduced pressure
  3. customThe crude residue is purified

Sources & evidence

ORD record
ord-c46479f8c8844a27a2770c714711f97c
Source dataset
uspto-grants-2004_08
Patent number
US06777431B2

Reaction notes

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