Potassium Carbonate → HCID 57168767, compound

HRID 1596461Notes

Reaction equation

HRID 1596461 reaction equation
[N+](C1C=C(S([O:13][CH2:14][C@:15]2([CH3:18])[CH2:17][O:16]2)(=O)=O)C=CC=1)([O-])=O.C([O-])([O-])=O.[K+].[K+].[C:25]([C:27]1[CH:32]=[CH:31][C:30](O)=[CH:29][CH:28]=1)#[N:26]>CC#N>[CH3:18][C@@:15]1([CH2:14][O:13][C:30]2[CH:31]=[CH:32][C:27]([C:25]#[N:26])=[CH:28][CH:29]=2)[CH2:17][O:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 86597620HCID 86597620, compound

Product 1

HCID 57168767HCID 57168767, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of [(2S)-2-methyloxiran-2-yl]methyl 3-nitro-1-benzenesulfonate (37.7 g; 138 mmol; from step (a) above), K2CO3 (28 g) and p-cyanophenol (23.8 g; 200 mmol) in MeCN (300 mL) was refluxed for 20 h. The reaction mixture was ffiltered and the filtrate concentrated under reduced pressure, dissolved in ether and washed with 2M NaOH and then brine. The organic layer was concentrated and subjected to column chromatography (petroleum ether:EtOAc; 3:1) to give the sub-title compound.

Workup

  1. temperaturewas refluxed for 20 h
  2. concentrationthe filtrate concentrated under reduced pressure
  3. dissolutiondissolved in ether
  4. washwashed with 2M NaOH
  5. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-f01ac1d2d811425fb8b4b79f78f1d2fc
Source dataset
uspto-grants-2001_09
Patent number
US06291475B1

Reaction notes

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