Water → N-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-2-nitro-benzenesulfonamide

HRID 2173752Notes

Reaction equation

HRID 2173752 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][CH2:14][CH2:15][O:16][C:17]1[CH:22]=[C:21]([C:23](OCC)=[O:24])[N:20]=[C:19]([C:28](OCC)=[O:29])[CH:18]=1)(=[O:12])=[O:11])([O-:3])=[O:2].[BH4-].[Na+].[Cl-].[Cl-].[Ca+2].O>C(O)C>[OH:24][CH2:23][C:21]1[CH:22]=[C:17]([O:16][CH2:15][CH2:14][NH:13][S:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])[CH:18]=[C:19]([CH2:28][OH:29])[N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 66714285Diethyl 4-[2-(2-nitro-benzenesulfonylamino)-ethoxy]-pyridine-2,6-dicarboxylate

Product 1

HCID 66713939N-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-2-nitro-benzenesulfonamideYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.3 g of diethyl 4-[2-(2-nitro-benzenesulfonylamino)-ethoxy]-pyridine-2,6-dicarboxylate in 200 mL of ethanol was successively added 315 mg of sodium borohydride and 941 mg of CaCl2. The mixture was stirred for 1 hour 30 minutes at room temperature and 50 ml of water were then added thereto. The ethanol was removed under reduced pressure and 50 ml of water were added to the residue obtained; the aqueous phase was extracted 3× with EtOAc. The organic phases were combined, washed with saturated NaCl solution, dried over MgSO4 and concentrated under reduced pressure. 1.06 g of N-[2-(2,6-bis-hydroxymethyl-pyridin-4-yloxy)-ethyl]-2-nitro-benzenesulfonamide were obtained. LC/MS (A): tr=0.57 min; [M+H]+: m/z 384.

Workup

  1. customThe ethanol was removed under reduced pressure and 50 ml of water
  2. additionwere added to the residue
  3. customobtained
  4. extractionthe aqueous phase was extracted 3× with EtOAc
  5. washwashed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c1f3f4d3725748f0bb00aaec3148301a
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

Loading…