Potassium Carbonate → HCID 53659221, compound

HRID 2414634Notes

Reaction equation

HRID 2414634 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][N:7]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[C:24][CH3:25])=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Br:32][C:33]1[CH:40]=[CH:39][C:36]([CH2:37]Br)=[CH:35][CH:34]=1>CN(C=O)C.CCOCC.O>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][N:10]([CH2:37][C:36]2[CH:39]=[CH:40][C:33]([Br:32])=[CH:34][CH:35]=2)[CH2:9][CH2:8][N:7]1[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]#[C:24][CH3:25])=[CH:17][CH:16]=1)(=[O:13])=[O:14])=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 54175880HCID 54175880, compound

Product 1

HCID 53659221HCID 53659221, compoundYield 99.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.30 g (0.820 mmol) of 1-(4-but-2-ynyloxy-benzenesulfonyl)-piperazine-2-carboxylic acid ethyl ester (Step 1, Example 220) in 10 mL of DMF was added 0.339 g (2.459 mmol) of potassium carbonate followed by 0.205 g (0.820 mmol) of p-bromobenzyl bromide. The reaction was stirred at room temperature for 15 h, then diluted with ether and water. The organics were washed with water, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:1) to provide 0.438 g of 4-(4-bromo-benzyl)-1-(4-but-2-ynyloxy-benzenesulfonyl)-piperazine-2-carboxylic acid ethyl ester as a colorless oil. Electrospray Mass Spec 534.9, 536.8 (M+H)+

Workup

  1. washThe organics were washed with water
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-b0d976c6a50a42eea35ce31200df19c0
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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