Water → 6-(tert-Butoxycarbonylamino-methyl)-nicotinic acid

HRID 347631Notes

Reaction equation

HRID 347631 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.O.[OH-].[Li+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 21083282HCID 21083282, compound

Product 1

HCID 218354266-(tert-Butoxycarbonylamino-methyl)-nicotinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 6-(tert-butyloxycarbonylaminomethyl)nicotinate from Example G3 (1.56 g, 5.84 mmol) in THF (20 ml) and water (5 ml) was added lithium hydroxide monohydrate (0.37 g, 8.76 mmol). The mixture was stirred at room temperature for 18 h and then concentrated in vacuo. The aqueous residue was acidified by addition of 1M citric acid solution and extracted with chloroform/IPA (3 times). The combined organic extracts were washed with brine, dried over MgSO4, and evaporated in vacuo to give a white solid; yield 1.38 g (94%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe aqueous residue was acidified by addition of 1M citric acid solution
  3. extractionextracted with chloroform/IPA (3 times)
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customto give a white solid

Sources & evidence

ORD record
ord-b3abb23d58434fa19710a21f1d4a47fb
Source dataset
uspto-grants-2007_02
Patent number
US07176195B2

Reaction notes

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