Hydrochloric Acid → HCID 18960399, compound

HRID 1707936Notes

Reaction equation

HRID 1707936 reaction equation
CC([NH:5][S:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][O:20]C2CCCCO2)[C:10]=1[C:27]([OH:29])=[O:28])(=[O:8])=[O:7])(C)C.Cl>CC(C)=O>[NH2:5][S:6]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][OH:20])[C:10]=1[C:27]([OH:29])=[O:28])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18960410HCID 18960410, compound

Product 1

HCID 18960399HCID 18960399, compoundYield 114.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 50 mL acetone plus 1.80 g (4.2 mmol) of 3-[[(1,1-dimethylethyl)amino]sulfonyl]-1-[2-(tetrahydro-2-pyranyloxy)ethyl]1H-indole-2-carboxylic acid was added 4.2 mL 1N HCl and the mixture was stirred overnight. Acetone was then evaporated and the residue extracted with ethyl acetate three times. The organic layer was washed once with brine, dried (Na2SO4) and stripped to dryness. The residue was then taken up in trifluoroacetic acid (20 mL) then evaporated in vacuo after several hours at room temperature. The residue was triturated and collected with ethyl ether to afford 1.37 g of the title compound, m.p. 145°-146° C. dec.

Workup

  1. customAcetone was then evaporated
  2. extractionthe residue extracted with ethyl acetate three times
  3. washThe organic layer was washed once with brine
  4. dry with materialdried (Na2SO4)
  5. customthen evaporated in vacuo after several hours at room temperature
  6. customThe residue was triturated
  7. customcollected with ethyl ether

Sources & evidence

ORD record
ord-a9512230f8944670a7908364f86e1bb3
Source dataset
uspto-grants-1994_10
Patent number
US05356862

Reaction notes

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