Ammonium Chloride → HCID 77333168, compound

HRID 1439957Notes

Reaction equation

HRID 1439957 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][CH:16]2[CH:10]3[CH:11]([O:12][C:13]4[C:5]([OH:4])=[CH:6][CH:7]=[CH:8][C:9]=43)[CH2:14][CH: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 86749318HCID 86749318, compound

Product 1

HCID 77333168HCID 77333168, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The (1S, 2S, 3aR, 8bS)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl acetate (1.14 g), produced according to the process described above, was dissolved in methanol (15 ml) followed by the addition of 0.61N potassium hydroxide/methanol solution (5.0 ml) and stirring for 30 minutes at room temperature. The reaction mixture was added to a 5% aqueous solution of ammonium chloride and extracted with ethyl acetate (60 ml+30 ml×2). The organic layer was washed with saturated brine (30 ml) and concentrated to a solid after drying with anhydrous sodium sulfate. The residue was purified with column chromatography (silica gel: chloroform/methanol 20:1-10:1) to obtain (1SR, 2S, 3aR, 8bS)-1-benzenesulfonamido-2-hydroxy-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-ol (940 mg).

Workup

  1. extractionextracted with ethyl acetate (60 ml+30 ml×2)
  2. washThe organic layer was washed with saturated brine (30 ml)
  3. concentrationconcentrated to a solid
  4. dry with materialafter drying with anhydrous sodium sulfate
  5. customThe residue was purified with column chromatography (silica gel: chloroform/methanol 20:1-10:1)

Sources & evidence

ORD record
ord-0d812dd9834349c3a025a77cbb6d4cec
Source dataset
uspto-grants-1996_03
Patent number
US05496849

Reaction notes

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