Sulfuric Acid → HCID 71548692, compound

HRID 1526520Notes

Reaction equation

HRID 1526520 reaction equation
[CH2:1]([C@:8]1([C:23]([NH:25][CH2:26][C:27](=O)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:24])[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>C(=O)([O-])O.[Na+]>[CH2:1]([C@:8]1([C:23]2[O:24][C:27]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:26][N:25]=2)[O:12][C:11](=[O:13])[N:10]([C@@H:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:15])[C:9]1=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 90407993HCID 90407993, compound

Product 1

HCID 71548692HCID 71548692, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To the product of Step B (40 mg, 0.088 mmol) was added concentrated sulfuric acid (0.5 mL, 9.38 mmol) and the mixture stirred for 16 h. Ice was added followed by saturated aqueous sodium hydrogen carbonate (30 mL) and the mixture was extracted with ethyl acetate (3×10 mL). The combined organic fractions were washed with saturated aqueous brine (1×15 mL), dried with anhydrous sodium sulfate, filtered and the solvent removed in vacuo. The yellow oil was purified by reverse phase HPLC(YMC Pro-C 18 column, gradient elution, 20% to 100% acetonitrile/water with 0.1% TFA) to afford the title compound as a colorless amorphous solid. LC/MS 439.1 (M+1). IC50 value=C rating

Workup

  1. additionIce was added
  2. extractionthe mixture was extracted with ethyl acetate (3×10 mL)
  3. washThe combined organic fractions were washed with saturated aqueous brine (1×15 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe yellow oil was purified by reverse phase HPLC(YMC Pro-C 18 column, gradient elution, 20% to 100% acetonitrile/water with 0.1% TFA)

Sources & evidence

ORD record
ord-cc2a60cb9e1f4d7085410279826fe282
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

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