Water → HCID 53756535, compound

HRID 1976455Notes

Reaction equation

HRID 1976455 reaction equation
[N:1]1([C:7]([N:9]2[CH2:14][CH2:13][NH:12][CH:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:20]([O:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1)[C:21]#[C:22][CH3:23].O>N1C=CC=CC=1>[CH2:18]([O:17][C:15]([CH:11]1[CH2:10][N:9]([C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:8])[CH2:14][CH2:13][N:12]1[S:31]([C:28]1[CH:27]=[CH:26][C:25]([O:24][CH2:20][C:21]#[C:22][CH3:23])=[CH:30][CH:29]=1)(=[O:33])=[O:32])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 111959284-But-2-ynyloxy-benzenesulfonyl chlorideHCID 22644747HCID 22644747, compound

Product 1

HCID 53756535HCID 53756535, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

The ethyl 4-(4-morpholinylcarbonyl)-2-piperazinecarboxylate (0.41 g, 1.55 mmol) was dissolved in pyridine (1.44 mL). To this solution was added a solution of 4-but-2-ynyloxy-benzenesulfonyl chloride (0.38 g, 1.55 mmol) in pyridine (1 mL). The reaction was stirred overnight and then poured into water. The mixture was extracted three times with chloroform. The organics were combined, washed with 10% HCl, twice with water, then brine and dried over Na2SO4. The solution was filtered and concentrated in vacuo to provide 0.6 g (81%) of 1-(4but-2-ynyloxy-benzenesulfonyl)-4-(morpholine4-carbonyl)- piperazine-2-carboxylic acid ethyl ester as a gold oil. Electrospray Mass Spec 480.2 (M+H)+.

Workup

  1. extractionThe mixture was extracted three times with chloroform
  2. washwashed with 10% HCl, twice with water
  3. dry with materialbrine and dried over Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-56b141fa722949c393af859f3d71426f
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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