Lithium hydroxide, monohydrate → HCID 22644793, compound

HRID 1976456Notes

Reaction equation

HRID 1976456 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][N:10]([C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:13])[CH2:9][CH2:8][N:7]1[S:20]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[C:32][CH3:33])=[CH:25][CH:24]=1)(=[O:22])=[O:21])=[O:5])C.O.[OH-].[Li+]>C1COCC1.CO.O>[CH2:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([S:20]([N:7]2[CH2:8][CH2:9][N:10]([C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[O:13])[CH2:11][CH:6]2[C:4]([OH:5])=[O:3])(=[O:22])=[O:21])=[CH:28][CH:27]=1)[C:31]#[C:32][CH3:33]

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 53756535HCID 53756535, compound

Product 1

HCID 22644793HCID 22644793, compoundYield 55.9%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

The 1-(4-but-2-ynyloxy-benzenesulfonyl)-4-(morpholine-4-carbonyl)-piperazine-2-carboxylic acid ethyl ester (0.56 g, 1.18 mmol) was dissolved in THF/MeOH/H2O (3 mL each) and treated with lithium hydroxide monohydrate (0.099 g, 2.3 mmol). The reaction was heated at reflux overnight and then concentrated and acidified to pH 4 with acetic acid. The solution was extracted with methylene chloride and then washed with water, brine, dried over Na2SO4, filtered and concentrated in vacuo to provide 0.298 g (53%) of 1-(4-but-2-ynyloxy-benzenesulfonyl)-4-(morpholine-4-carbonyl)- piperazine-2-carboxylic acid as a yellow powder. Electrospray Mass Spec 452.2 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated
  4. extractionThe solution was extracted with methylene chloride
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b669ceee263402697cf8278cf324eb4
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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