HCID 11683006, compound → HCID 11683007, compound

HRID 2376167Notes

Reaction equation

HRID 2376167 reaction equation
Cl.Cl.[CH2:3]([N:10]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]2[N:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([NH:26][OH:27])=[O:25])=[CH:18][CH:17]=2)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C([O-])(O)=O.[Na+].O>[CH2:3]([N:10]1[CH2:14][CH2:13][C@@H:12]([NH:15][C:16]2[N:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([NH:26][OH:27])=[O:25])=[CH:18][CH:17]=2)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 11683006HCID 11683006, compound

Product 1

HCID 11683007HCID 11683007, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 516892Sodium BicarbonateCatalystHCID 962WaterSolvent

Procedure

(2E)-3-(6-{[(3R)-1-Benzyl-3-pyrrolidinyl]amino}-3-pyridyl)-N-hydroxyacrylamide dihydrochloride (860 mg) was dissolved into water (40 ml), and the solution was adjusted to ca. pH4.0 by addition of a few drops of aq NaHCO3 solution. The aqueous solution was chromatographed with HP-20 (100 ml), washing with water and eluting with 75% aqueous MeOH. The elute was concentrated to ca. 10 ml in vacuo, and the resulting precipitate was collected by filtration. (2E)-3-(6-{[(3R)-1-benzyl-3-pyrrolidinyl]amino}-3-pyridyl)-N-hydroxyacrylamide (240 mg) was obtained as colorless powder.

Workup

  1. customThe aqueous solution was chromatographed with HP-20 (100 ml)
  2. washwashing with water
  3. washeluting with 75% aqueous MeOH
  4. concentrationThe elute was concentrated to ca. 10 ml in vacuo
  5. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-f47c2bdcb567426385710ff3e295e723
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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