Sulfuric Acid → HCID 68867273, compound

HRID 2112785Notes

Reaction equation

HRID 2112785 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:18]=[C:17](CC3C=CC=CC=3)[CH:16]=[C:15]([OH:26])[C:8]=2[S:9][C:10]=1[NH:11]C(=O)C)=[O:5])[CH3:2].OS(O)(=O)=O>CO>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:18]=[CH:17][C:16]([CH2:6][C:7]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:8]=3)=[C:15]([OH:26])[C:8]=2[S:9][C:10]=1[NH2:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 59854635HCID 59854635, compound

Product 1

HCID 68867273HCID 68867273, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 02-6 (4.3 g, 11.7 mmol) was dissolved in MeOH (350 mL), conc. H2SO4 (2 mL) was added and the mixture was stirred for 8 days. The mixture was concentrated to half of the original volume. H2O was added and the pH was cautiously adjusted to 8 with conc. NH4OH. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (100 mL), brine (100 mL) and dried over Na2SO4. The solvent was removed in vacuo to give the crude product, which was purified by column chromatography (SiO2, EtOAc/hept=1/4+1% Et3N to 1/1). The product was obtained in only 80% purity according to HPLC and therefore subjected to automated column chromatography to give a-2 (2.1 g, 6.4 mmol, 55%) as a brown-yellow solid.

Workup

  1. concentrationThe mixture was concentrated to half of the original volume
  2. additionH2O was added
  3. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  4. washThe combined organic layers were washed with H2O (100 mL), brine (100 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a6a7f512cfb24328910338e003377f10
Source dataset
uspto-grants-2009_04
Patent number
US07524853B2

Reaction notes

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