Lithium hydroxide, monohydrate → HCID 21138910, compound

HRID 1359032Notes

Reaction equation

HRID 1359032 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][N:8]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[C@@H:7]([C:22](=[O:32])[NH:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:6]1)=[O:4].O.[OH-].[Li+]>CO.O>[CH2:25]([O:24][NH:23][C:22]([C@H:7]1[CH2:6][C@H:5]([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][N:8]1[S:11]([C:14]1[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=1)(=[O:13])=[O:12])=[O:32])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53855238HCID 53855238, compound

Product 1

HCID 21138910HCID 21138910, compound

Reagents, catalysts & solvents 1

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

Procedure

To a stirred cold (0° C.) solution of (2R,4R)-2-benzyloxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-piperidine-4-carboxylic acid methyl ester (4.0 g, 8.6 mmol) in 10 mL of 9:1 methanol/water was added lithium hydroxide monohydrate (1.8 g, 43 mmol). The mixture was stirred for 2 hours before Amberlite IR-120 resin (96 g) was added. After 15 minutes, the mixture was filtered and the filtrate was concentrated to give (2R,4R)-2-benzyloxycarbamoyl-1-(4-methoxy-benzenesulfonyl)-piperidine-4-carboxylicacid, which was used in the subsequent reaction without purification.

Workup

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

Sources & evidence

ORD record
ord-3c8bbfe87b704c9997845b4ab529a837
Source dataset
uspto-grants-2003_07
Patent number
US06599890B1

Reaction notes

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