Ammonium Chloride → HCID 86749317, compound

HRID 1439955Notes

Reaction equation

HRID 1439955 reaction equation
C([O:4][C:5]1[C:13]2[O:12][C@H:11]3[CH2:14][C@@H:15]([OH:27])[C@H:16]([NH:17][S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C@H:10]3[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=O)C.[OH-].[K+].CO.[Cl-].[NH4+]>CO>[C:21]1([S:18]([NH:17][C@@H:16]2[C@@H:10]3[C@@H:11]([O:12][C:13]4[C:5]([OH:4])=[CH:6][CH:7]=[CH:8][C:9]=43)[CH2:14][C@H:15]2[OH:27])(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23689386Potassium hydroxide methanolHCID 86749315HCID 86749315, compound

Product 1

HCID 86749317HCID 86749317, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The (1R, 2R, 3aS, 8bR)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl acetate (448 mg), produced according to the process described above, was dissolved in methanol followed by the addition of 0.61N potassium hydroxide/methanol solution (1.9 ml) and stirring for 20 minutes at room temperature. The reaction mixture was added to a 5% aqueous solution of ammonium chloride and extracted with ethyl acetate (50 ml+30 ml×2). The organic layer was washed with saturated brine (30 ml) and concentrated after drying with anhydrous sodium sulfate. The residue was purified with column chromatography (silica gel: methylene chloride/methanol 20:1-7:1) to obtain (1R, 2R, 3aS, 8bR)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta [b]benzofuran-5-ol (376 mg).

Workup

  1. extractionextracted with ethyl acetate (50 ml+30 ml×2)
  2. washThe organic layer was washed with saturated brine (30 ml)
  3. concentrationconcentrated
  4. dry with materialafter drying with anhydrous sodium sulfate
  5. customThe residue was purified with column chromatography (silica gel: methylene chloride/methanol 20:1-7:1)

Sources & evidence

ORD record
ord-d33e726859b74b71968457c9265fa547
Source dataset
uspto-grants-1996_03
Patent number
US05496849

Reaction notes

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