Sulfuric Acid → HCID 59854714, compound

Compound 03-6 (3.64 g, 10.9 mmol) was suspended in a mixture of MeOH (450 mL) and MeCN (100 mL). H2SO4 (1.5 mL) was added and the mixture was stirred under a N2-atmosphere, while monitoring the reaction by HPLC. After 7 days the conversion was complete and the mixture was concentrated to half of the original volume. Water 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 as a green sticky oil, which was purified by column chromatography (SiO2, EtOAc/Hept=1/4+1% Et3N). The product fractions were pooled and the solvent was removed in vacuo. The residue was dissolved in Et2O (50 mL) and the solution was washed with conc. aq. NH4Cl (2×50 mL) and brine (50 mL) to remove residual NEt3. After drying over Na2SO4, the solvent was removed in vacuo to give a-3 (2.6 g, 8.9 mmol, 82%) as a greenish grey solid.

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

ORD record

ord-1be6dda1cb864d9bbe8357cf7849b7bb

Source dataset

uspto-grants-2009_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07524853B2