Pyridine → HCID 58743868, compound

HRID 723314Notes

Reaction equation

HRID 723314 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[C:15]=2[OH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:22][CH2:23][S:24](Cl)(=[O:26])=[O:25].N1C=CC=CC=1>C1COCC1.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][S:24]([CH2:23][Cl:22])(=[O:26])=[O:25])[C:15]=2[OH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 77054(Chloromethyl)sulfonyl chlorideHCID 58743872HCID 58743872, compound

Product 1

HCID 58743868HCID 58743868, compoundYield 46.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a dry roundbottom flask, 4-(3-amino-2-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (293 mg., 1 mmol) was dissolved in dry THF (3 mL) under nitrogen. While stirring, chloro-methanesulfonyl chloride (149 mg., 1 mmol) was added dropwise over 10 minutes and the solution was stirred 30 minutes. Pyridine (0.121 mL., 1.5 mmol) was then added dropwise over 5 minutes and the solution was stirred for 18 hours. The reaction mixture was diluted with 40 mL Et2O and washed with 40 mL of 10% aqueous HCl, 50 mL water, and 50 mL brine. The organic fraction was dried over MgSO4 and concentrated in vacuo. The residue is purified by flash chromatography (20% to 40% EtOAc in hexanes) to give 190 mg of 4-(3-Chloromethanesulfonylamino-2-hydroxy-phenyl)-piperazine-1-carboxylic acid tert-butyl ester as an amber oil (45%). (M−H)−=404.

Workup

  1. stirringthe solution was stirred 30 minutes
  2. stirringthe solution was stirred for 18 hours
  3. washwashed with 40 mL of 10% aqueous HCl, 50 mL water, and 50 mL brine
  4. dry with materialThe organic fraction was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (20% to 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ed425fc9c2a74fd79f921a96be6054d2
Source dataset
uspto-grants-2006_11
Patent number
US07141562B2

Reaction notes

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