Hydrochloric Acid → HCID 19981723, compound

HRID 1460415Notes

Reaction equation

HRID 1460415 reaction equation
[CH2:1]([S:5][C:6]([CH3:35])([CH3:34])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][CH:12]([CH2:26][N:27]1[CH2:32][CH2:31][CH:30]([CH3:33])[CH2:29][CH2:28]1)[C:13]([S:16]CC1C=CC(OC)=CC=1)([CH3:15])[CH3:14])[CH2:2][CH2:3][CH3:4].FC(F)(F)S(O)(=O)=O.O1CCCC1.Cl.O1CCOCC1>CCOCC>[CH2:1]([S:5][C:6]([CH3:34])([CH3:35])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][CH:12]([CH2:26][N:27]1[CH2:28][CH2:29][CH:30]([CH3:33])[CH2:31][CH2:32]1)[C:13]([SH:16])([CH3:15])[CH3:14])[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 312751,4-DioxaneHCID 62406Trifluoromethanesulfonic acidHCID 70397628HCID 70397628, compound

Product 1

HCID 19981723HCID 19981723, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of Compound (32) (HCl salt) (2.5 g; 4.2 mmol) in a 1M trifluoromethanesulfonic acid in tetrahydrofuran (42 ml; 42 mmol) was stirred for 1 hour under cooling. The reaction mixture was combined with ether and extracted with 2N hydrochloric acid five times. The aqueous layer was adjusted to pH 10 with potassium carbonate and extracted with chloroform three times. The chloroform extract was washed with a saturated aqueous sodium chloride solution two times, dried over anhydrous sodium sulfate and concentrated. Under cooling, a 4N hydrogen chloride in dioxane (7 ml; 28 mmol) was added thereto, followed by concentration. The residue was purified by silica gel column chromatography with a mixture of chloroform and methanol (20:1) as an eluting solvent to give Compound (33) (HCl salt) (0.5 g; yield, 24%).

Workup

  1. temperatureunder cooling
  2. extractionextracted with 2N hydrochloric acid five times
  3. extractionextracted with chloroform three times
  4. extractionThe chloroform extract
  5. washwas washed with a saturated aqueous sodium chloride solution two times
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. temperatureUnder cooling
  9. concentrationfollowed by concentration
  10. customThe residue was purified by silica gel column chromatography with a mixture of chloroform and methanol (20:1) as an eluting solvent

Sources & evidence

ORD record
ord-49ef18edddda4db9a23ecec8703e9797
Source dataset
uspto-grants-1991_12
Patent number
US05071636

Reaction notes

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