Water → HCID 66848435, compound

HRID 389609Notes

Reaction equation

HRID 389609 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:17]([O:24][C:25](Cl)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CC(C)=O.O.C(Cl)Cl>[CH2:17]([O:24][C:25]([NH:1][C:2]1[N:7]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[CH:5]=[CH:4][CH:3]=1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 13809143Methyl 6-aminopyridine-2-carboxylate

Product 1

HCID 66848435HCID 66848435, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 6-aminopicolinate (10.65 g, 70 mmol, 1 eq) and sodium bicarbonate (13 g, 154 mmol, 2.2 eq) was dissolved in a mixture of acetone/water (2:1, 1M), and the solution cooled to 0° C. Benzyloxycarbonyl chloride (Cbz-Cl, 11.3 ml, 80.5 mmol, 1.15 eq) was added dropwise, and the reaction was warmed to room temperature and stirred for 18 hours. Water (200 mL) was added, and the resultant suspension was filtered to give a white solid. This solid was dissolved in methylene chloride, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide methyl 6-(benzyloxycarbonylamino)picolinate (17.5 g).

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. filtrationthe resultant suspension was filtered
  3. customto give a white solid
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5550b9d67e044c3591041e79c960210c
Source dataset
uspto-grants-2013_02
Patent number
US08378108B2

Reaction notes

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