Imidazole → HCID 59279535, compound

A solution of tert-butylchlorodimethylsilane (661 mg, 4.38 mmol) in DMF (2.5 mL) was added dropwise to a stirred solution of (S)-methyl 2-hydroxy-3-methoxypropanoate C4a (490 mg, 3.65 mmol) and 1H-imidazole (497 mg, 7.31 mmol) in DMF (5 mL) at 20° C., over a period of 2 minutes. The resulting solution was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated, diluted with EtOAc (50 mL) and washed sequentially with water (4×15 mL) and saturated brine (20 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. Purification by flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane afforded (S)-methyl 2-(tert-butyldimethylsilyloxy)-3-methoxypropanoate (750 mg).

1. concentrationThe reaction mixture was concentrated
2. additiondiluted with EtOAc (50 mL)
3. washwashed sequentially with water (4×15 mL) and saturated brine (20 mL)
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customto afford crude product
8. customPurification
9. washby flash silica chromatography, elution gradient 20 to 50% EtOAc in isohexane

ORD record

ord-5dbe31d3df4e41b3906f2fe7e3314d53

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143263B2