Methanol → HCID 53962807, compound

HRID 1359038Notes

Reaction equation

HRID 1359038 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([CH2:14][CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)(=[O:13])=[O:12])[C@@H:7]([C:25](=[O:28])[NH:26][OH:27])[CH2:6]1)=[O:4].O.[OH-].[Li+].CO>CO.O>[F:24][C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:16][CH2:15][CH2:14][S:11]([N:8]2[CH2:9][CH2:10][C@@H:5]([C:3]([OH:4])=[O:2])[CH2:6][C@@H:7]2[C:25](=[O:28])[NH:26][OH:27])(=[O:13])=[O:12])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 53990110HCID 53990110, compound

Product 1

HCID 53962807HCID 53962807, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a stirred, cold (0° C.) solution of (2R,4R)-1-[3-(4-fluorophenoxy)-propane-1-sulfonyl]-2-hydroxycarbamoyl-piperidine-4-carboxylic acid methyl ester (400 mg, 0.96 mmol) in 5 mL of a methanol/water mixture (10:1) was added lithium hydroxide monohydrate (120 mg, 2.88 mmol). After 3 hours at 0° C., prerinsed (methanol) Amberlite resin (4.1 g) was added. The mixture was filtered and the filtrate was concentrated to give 370 mg of (2R,4R)-1-[3-(4-fluorophenoxy)-propane-1-sulfonyl]-2-hydroxycarbamoyl-piperidine-4-carboxylic acid as a white foam: MS (atmospheric pressure chemical ionization) acidic mode, 403 (M−1).

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a074b9ef2dc8467598df32f9470799a4
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

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