Lithium hydroxide, monohydrate → HCID 59253185, compound

HRID 1809395Notes

Reaction equation

HRID 1809395 reaction equation
C([O:3][C:4](=[O:21])[C:5]([S:8]([CH:11]1[CH2:16][CH2:15][N:14]([S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][CH2:12]1)(=[O:10])=[O:9])([CH3:7])[CH3:6])C.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:20][S:17]([N:14]1[CH2:13][CH2:12][CH:11]([S:8]([C:5]([CH3:7])([CH3:6])[C:4]([OH:21])=[O:3])(=[O:9])=[O:10])[CH2:16][CH2:15]1)(=[O:18])=[O:19]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59253292HCID 59253292, compound

Product 1

HCID 59253185HCID 59253185, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a suspension of 2.91 g (8.53 mmol) of 2-(1-methanesulfonyl-piperidine-4-sulfonyl)-2-methyl-propionic acid ethyl ester in THF/water (1/1, 60 mL) are added 2.56 g (34.13 mmol) of lithium hydroxide monohydrate. The reaction is stirred at room temperature for 3 d and then concentrated under reduced pressure. The residue is partitioned between brine (20 mL) and DCM (20 mL). The aqueous layer is further acidified with 2M aqueous HCl solution to pH 1 and extracted with DCM. The combined organic extracts are concentrated under reduced pressure to afford 1.68 g of 2-(1-methanesulfonyl-piperidine-4-sulfonyl)-2-methyl-propionic acid. Yield 63%, ES-MS: 314 [M+H]; 1H NMR (500 MHz, MeOD) δ ppm 1.66 (6H, s), 1.86-1.97 (2H, m), 2.24 (2H, dd, J=13.64, 2.54 Hz), 2.87 (3H, s), 2.92 (2H, td, J=12.00, 2.59 Hz), 3.81 (2H, dt, J=12.45, 3.13 Hz), 3.94 (1H, tt, J=11.41, 3.79 Hz)

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is partitioned between brine (20 mL) and DCM (20 mL)
  3. extractionextracted with DCM
  4. concentrationThe combined organic extracts are concentrated under reduced pressure

Sources & evidence

ORD record
ord-220ca99a923140e6b258eecc92fc3d14
Source dataset
uspto-grants-2013_01
Patent number
US08362039B2

Reaction notes

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