Ethylene Glycol → HCID 22710203, compound

HRID 352883Notes

Reaction equation

HRID 352883 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6]([S:20]([N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:25]([CH2:36][CH:37]=[O:38])[CH2:24]1)(=[O:22])=[O:21])=[CH:5]2.[CH2:39](O)[CH2:40][OH:41].CC1C=CC(S(O)(=O)=O)=CC=1.O.C(OCC)(=O)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])[C:6]([S:20]([N:23]1[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH:25]([CH2:36][CH:37]3[O:41][CH2:40][CH2:39][O:38]3)[CH2:24]1)(=[O:21])=[O:22])=[CH:5]2

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 22709577HCID 22709577, compound

Product 1

HCID 22710203HCID 22710203, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

In toluene (10 mL) were dissolved 4-[(5-chloro-1-phenylsulfonylindol-2-yl)sulfonyl]-1-(tert-butoxycarbonyl)-2-(formylmethyl)piperazine (440 mg) and ethylene glycol (71 mg, followed by the addition of p-TsOH.H2O (15 mg). The resulting mixture was heated to 60° C. and stirred for 16 hours. Ethyl acetate was added to the reaction mixture. The resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was dried over anhydrous MgSO4 and distilled under reduced pressure to remove the solvent, whereby the title compound (460 mg) was obtained as colorless amorphous.

Workup

  1. washThe resulting mixture was washed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. distillationdistilled under reduced pressure
  4. customto remove the solvent, whereby the title compound (460 mg)
  5. customwas obtained as colorless amorphous

Sources & evidence

ORD record
ord-c6c5e0b01ac64504af4c8ef5d773d6d0
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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