Water → HCID 53756535, compound

HRID 2414625Notes

Reaction equation

HRID 2414625 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-(4-but-2-ynyloxy- benzenesulfonyl)-4-(morpholine-4-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-0b7c40d081a441caadf6453f4bb64c4e
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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