HCID 21064711, compound → HCID 21928101, compound

HRID 1243781Notes

Reaction equation

HRID 1243781 reaction equation
C[O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:20])[CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:6][CH:5]=1>CO>[C:16]([O:15][C:13]([NH:12][CH2:11][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:21])=[O:2])=[CH:5][N:6]=1)[OH:20])=[O:14])([CH3:19])([CH3:17])[CH3:18]

Participants

3

Reactant 1

HCID 21064711HCID 21064711, compound

Product 1

HCID 21928101HCID 21928101, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(2-tert-Butoxycarbonylamino-1-hydroxy-ethyl)-nicotinic acid methyl ester (137.3 mg, 0.450 mmol) was dissolved into 3 mL of MeOH. To this was added LiOH monohydrate (56.5, 1.350 mmol). The reaction stirred at room temperature overnight. The reaction mixture was concentrated on a rotary evaporator, dissolved into 2 mL of water, and brought to pH 4 with AcOH. The mixture was extracted into 3×10 mL of EtOAc and the organic fractions combined. The organic phase was washed with 2×20 mL H2O and 1×20 mL of brine, dried MgSO4, filtered and concentrated to give 130 mg of 6-(2-tert-butoxycarbonylamino-1-hydroxy-ethyl)-nicotinic acid.

Workup

  1. concentrationThe reaction mixture was concentrated on a rotary evaporator
  2. dissolutiondissolved into 2 mL of water
  3. extractionThe mixture was extracted into 3×10 mL of EtOAc
  4. washThe organic phase was washed with 2×20 mL H2O and 1×20 mL of brine, dried MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31ed82f9e1304e4c85f505a703bd740d
Source dataset
uspto-grants-2006_10
Patent number
US07119102B2

Reaction notes

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