Lithium Hydroxide → 3-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-carboxymethyl-pyridin-3-yl)-benzoic acid

HRID 554585Notes

Reaction equation

HRID 554585 reaction equation
C([O:8][C:9](=[O:40])[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=2)=[C:12]([CH2:26][N:27]([C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:28][CH3:29])[CH:11]=1)C1C=CC=CC=1.[Li+].[OH-]>CO>[CH2:33]([O:32][C:30]([N:27]([CH2:26][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[C:16]1[CH:17]=[N:18][CH:19]=[C:20]([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=1)[C:9]([OH:40])=[O:8])[CH2:28][CH3:29])=[O:31])[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 585650203-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-carboxymethyl-pyridin-3-yl)-benzoic acid benzyl ester

Product 1

HCID 451025933-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-carboxymethyl-pyridin-3-yl)-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

3-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-carboxymethyl-pyridin-3-yl)-benzoic acid benzyl ester (0.369 g, 0.68 mmol) was dissolved in MeOH (4 mL) and cooled to 0° C. 1N Aqueous LiOH (3 mL, 3 mmol) was added, and the reaction was stirred at room temperature for 1 hour. The mixture was quenched with 1N aqueous HCl (3 mL) and extracted with EtOAc. The combined organic layers were washed with H2O and concentrated, and the residue was purified by preparative HPLC to give Compound 1.

Workup

  1. customThe mixture was quenched with 1N aqueous HCl (3 mL)
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with H2O
  4. concentrationconcentrated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cb6f8039faf34338b5256942566cab47
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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