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

HRID 2173752노트

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HRID 2173752 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c1f3f4d3725748f0bb00aaec3148301a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056914B2

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