3-Hydroxypyridine → HCID 23368445, compound

HRID 1901596Notes

Reaction equation

HRID 1901596 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:21][OH:22])[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:21][O:22][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH2:10][O:11][C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23368567HCID 23368567, compound

Product 1

HCID 23368445HCID 23368445, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.5 g of 3-(2-tert-butoxycarbonylamino-3-hydroxypropoxy)-1,2-benzoisoxazole in 5 ml of tetrahydrofuran are added 0.154 g of 3-hydroxypyridine, 0.553 g of triphenylphosphine and 0.33 ml of diethyl azodicarboxylate at room temperature with ice-cooling, and they are subjected to reaction at room temperature for eight hours. The solvent is removed from the reaction mixture by distillation under reduced pressure, and the residue obtained is purified by a silica gel column chromatography [eluant:n-hexane:ethyl acetate=4:1], to obtain 0.32 g of oily 3-[2-tert-butoxycarbonylamino-3-(3-pyridyloxy)propoxy]-1,2-benzoisoxazole.

Workup

  1. temperaturecooling
  2. customthey are subjected to reaction at room temperature for eight hours
  3. customThe solvent is removed from the reaction mixture by distillation under reduced pressure
  4. customthe residue obtained
  5. customis purified by a silica gel column chromatography [eluant:n-hexane:ethyl acetate=4:1]

Sources & evidence

ORD record
ord-77812c50be0b4823b1cfc229bc8e1770
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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