HCID 54757208, compound → HCID 54757202, compound

HRID 632522Notes

Reaction equation

HRID 632522 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH2:24][CH:25]3[CH2:27][S:26]3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:10][C:9]=1[O:28]COC)(C)(C)C>CO.Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([S:21]([CH2:24][CH:25]3[CH2:27][S:26]3)(=[O:23])=[O:22])=[CH:19][CH:20]=2)=[CH:10][C:9]=1[OH:28]

Participants

4

Reactant 1

HCID 54757208HCID 54757208, compound

Product 1

HCID 54757202HCID 54757202, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 21 (0.10 mg, 0.21 mmol) in methanol (5 mL) was added a few drops of conc. HCl. After the mixture was stirred at reflux for 1 h, the solvent was evaporated in vacuo. The crude product was taken up into water and EtOAc. Layers were separated and the aqueous layer was washed with EtOAc. The combined organic layers were dried over anhydrous Na2SO4, the suspension was filtered and the filtrate was concentrated in vacuo. Purification by silica gel chromatography (hexanes/EtOAc=1/1) gave 22 in 95% yield (66 mg). 1H NMR (500 MHz, CDCl3) 82.14 (dd, J=1.3, 4.9 Hz, 1H), 2.18 (d, J=1.0 Hz, 1H), 2.56-2.49 (m, 1H), 3.08-3.00 (m, 1H), 3.17 (dd, J=7.8, 14.4 Hz, 1H), 3.51 (dd, J=5.6, 14.2 Hz, 2H), 6.54-6.46 (m, 2H), 6.80-6.73 (m, 1H), 7.07-6.97 (m, 2H), 7.80 (m, 2H). 13C NMR (126 MHz, CDCl3) δ 24.4, 26.3, 62.8, 108.5, 113.1, 117.2, 117.9, 130.7, 131.1, 131.9, 145.9, 147.3, 164.1. HRMS (FAB) calcd for C15H16NO4S2 (M+H+) 338.0515. found 338.0507.

Workup

  1. temperatureat reflux for 1 h
  2. customthe solvent was evaporated in vacuo
  3. customLayers were separated
  4. washthe aqueous layer was washed with EtOAc
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationthe suspension was filtered
  7. concentrationthe filtrate was concentrated in vacuo
  8. customPurification by silica gel chromatography (hexanes/EtOAc=1/1)

Sources & evidence

ORD record
ord-daaeb39d655b41d5918b7153a30d670e
Source dataset
uspto-grants-2016_04
Patent number
US09321754B2

Reaction notes

Loading…