Hydrochloric Acid → HCID 23633475, compound

HRID 913339Notes

Reaction equation

HRID 913339 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([C@H:15]([NH:17][S:18]([C:21]2[O:25][C:24]([C:26]([O:28]C)=[O:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH3:16])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CC(O)=O>[C:1]([C:9]1[CH:10]=[C:11]([C@H:15]([NH:17][S:18]([C:21]2[O:25][C:24]([C:26]([OH:28])=[O:27])=[CH:23][CH:22]=2)(=[O:20])=[O:19])[CH3:16])[CH:12]=[CH:13][CH:14]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 16112807HCID 16112807, compound

Product 1

HCID 23633475HCID 23633475, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 5-({[(1R)-1-(3-benzoylphenyl)ethyl]amino}sulfonyl)-2-furoate (0.1 g, 0.24 mmol) in glacial AcOH (10 mL) few drops of 37% HCl were added and the resulting solution was refluxed for 12 h. After cooling at room temperature solvents were evaporated under vacuum, the residue was diluted with a saturated solution of NaHCO3 (10 mL), washed with CHCl3 (2×5 mL), acidified to pH 1 by 37% HCl and extracted again with CHCl3 (2×5 mL). The collected organic extracts were dried over Na2SO4, filtered and evaporated under vacuum to give the pure compound 11 as a waxy solid (0.075 g, 78% yield). [α]D25 (c=0.5, CH2Cl2): −12°; 1H-NMR (CDCl3) δ 7.75 (d, 2H, J=7 Hz), 7.60 (d, 3H, J=7 Hz), 7.50-7.35 (m, 3H), 7.30 (m, 1H), 7.05 (d, 1H, J=7 Hz), 6.85 (d, 1H, J=7 Hz), 5.75 (bs, 1H, NH), 4.78 (q, 1H, J=7 Hz), 4.50 (bs, 1H, COOH), 1.57 (d, 3H, J=7 Hz).

Workup

  1. temperaturethe resulting solution was refluxed for 12 h
  2. customwere evaporated under vacuum
  3. additionthe residue was diluted with a saturated solution of NaHCO3 (10 mL)
  4. washwashed with CHCl3 (2×5 mL)
  5. extractionextracted again with CHCl3 (2×5 mL)
  6. dry with materialThe collected organic extracts were dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-fba382f7b7ba4a8ea22bc72ebe85e353
Source dataset
uspto-grants-2011_09
Patent number
US08026367B2

Reaction notes

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