Sulfuric Acid → HCID 86657248, compound

To methyl acetate (0.600 g, 8.1 mmol) and Ti(O-iPr)4 (0.15 g, 0.43 mmol) in ether (30 mL) was added dropwise EtMgBr (3.0M in ether, 6.0 mL, 18 mmol) over a hour period. After stirring for 20 minutes, the mixture was poured onto 10% H2SO4 (80 mL) and extracted with ether. The ether was dried over MgSO4 and concentrated in vacuo (0° C.) to one-quarter volume. The resulting solution was diluted with MeCN (20 mL) and treated with disuccinimidyl carbonate (4.15 g, 16.2 mmol). After stirring for an additional 20 minutes. Et3N (3.4 mL, 25 mmol) was added. After stilling for an additional 24 hours, the mixture was partitioned with EtOAc and saturated NaHCO3, dried over MgSO4, filtered and concentrated in vacuo to provide 1-methylcyclopropyl hydroxysuccinimidyl carbonate as a yellow solid (0.191 g, 0.90 mmol) which was combined with compound 77A (0.190 g, 0.45 mmol) and Et3N (0.25 mL, 1.8 mmol) in CH2Cl, (5 mL). After stirring for 1 h, the reaction was concentrated and purified using PLC to provide compound 311 as a yellow solid.

1. extractionextracted with ether
2. dry with materialThe ether was dried over MgSO4
3. concentrationconcentrated in vacuo (0° C.) to one-quarter volume
4. additionThe resulting solution was diluted with MeCN (20 mL)
5. stirringAfter stirring for an additional 20 minutes
6. waitAfter stilling for an additional 24 hours
7. customthe mixture was partitioned with EtOAc and saturated NaHCO3
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo

ORD record

ord-53e89dbe08734a81a65c6aadc57035cd

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08907095B2