Lithium Chloride → HCID 18739120, compound

HRID 1934681Notes

Reaction equation

HRID 1934681 reaction equation
[O:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:6][NH:7][C:8](=[O:28])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][C@@H:19]([C:24](OC)=[O:25])[CH2:20][CH2:21][S:22][CH3:23])[CH3:2].[Cl-].[Li+].[BH4-].[Na+]>O1CCCC1.C(O)C>[O:1]([C:3]1[CH:4]=[C:5]([CH:29]=[CH:30][C:31]=1[O:32][CH3:33])[CH2:6][NH:7][C:8](=[O:28])[C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[NH:18][C@@H:19]([CH2:24][OH:25])[CH2:20][CH2:21][S:22][CH3:23])[CH3:2]

Participants

6

Reactant 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 18739121HCID 18739121, compound

Product 1

HCID 18739120HCID 18739120, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3,4-dimethoxylbenzyl)-2-[(R)-1-methoxycarbonyl-3-(methylthio)propylamino]-5-nitrobenzamide (175 mg) in anhydrous tetrahydrofuran (3 mL) were added lithium chloride (31 mg), and then sodium borohydride (28 mg) in ethanol (3 mL) at ambient temperature. The mixture was stirred for one day. After evaporation of the solvent, the residue was partitioned between ethyl acetate and 10% citric acid aqueous solution. The separated organic layer was washed with water and brine and dried over magnesium sulfate. The residual solid was recrystallized from ethyl acetate-hexane to give N-(3,4-dimethoxylbenzyl)-2-[(R)-1-hydroxymethyl-3-(methylthio)propylamino]-5-nitrobenzamide (122 mg).

Workup

  1. customat ambient temperature
  2. customAfter evaporation of the solvent
  3. customthe residue was partitioned between ethyl acetate and 10% citric acid aqueous solution
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe residual solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-03a60829e56a45d5ba328ad54aa11a04
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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