Hydrochloric Acid → HCID 178437260, compound

HRID 41145Notes

Reaction equation

HRID 41145 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]3[CH2:25][C:24]([O:26]CC(C)C)=[C:23]([CH2:31][CH3:32])[C:22]3=[O:33])[CH:15]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH:21]3[CH2:25][C:24]([OH:26])=[C:23]([CH2:31][CH3:32])[C:22]3=[O:33])[CH:15]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 547577694-Chloro-N-(3-((3-ethyl-4-isobutoxy-2-oxocyclopent-3-en-1-yl)methyl)phenethyl)-benzenesulfonamide

Product 1

HCID 178437260HCID 178437260, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 38 (0.005 g, 0.11 mmol) in acetone (5 mL) was added with 2 N hydrochloric acid (5 mL). The reaction mixture was stirred at rt for 13 h and then concentrated, extracted with ethyl acetate (10 mL×2), and washed with brine (5 mL×2). The organic layer was dried with sodium sulfate anhydrous, filtered and concentrated and the residue so obtained was purified by reverse phase preparative HPLC to give the desired compound.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate (10 mL×2)
  3. washwashed with brine (5 mL×2)
  4. dry with materialThe organic layer was dried with sodium sulfate anhydrous
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue so obtained
  8. customwas purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-d81b282be2574cb49f99b68b5a49b3dd
Source dataset
uspto-grants-2013_09
Patent number
US08530520B2

Reaction notes

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