Pivaloyl chloride → HCID 14328129, compound

Triethylamine (3.50 ml, 25 mM) was added to compound 037 (4.90 g, 25 mM) dissolved in tetrahydrofuran (50 ml) and pivaloyl chloride (3.05 g, 25 mM) was added dropwise at -5° C., then the mixture was stirred for 30 minutes. Chloroform (50 ml) in solution with 2-chloroethylamine hydrochloride (2.90 g, 25 mM) and triethylamine (3.9 ml, 28 mM) was added dropwise thereto, then the mixture was stirred for 4 hours while slowly reaching room temperature. The reaction mixture was concentrated in vacuo, the residue was dissolved in chloroform and washed with dilute aqueous potassium carbonate. The aqueous layer was extracted with chloroform. The organic layer was combined, dried with anhydrous magnesium sulfate, and concentrated in vacuo. The residue was charged on a column of silica gel (C-200, 40 g), and eluted successively with chloroform and chloroformmethanol (20:1) to obtain the product (5.66 g, yield: 7.5%).

1. stirringthe mixture was stirred for 4 hours
2. customwhile slowly reaching room temperature
3. concentrationThe reaction mixture was concentrated in vacuo
4. dissolutionthe residue was dissolved in chloroform
5. washwashed with dilute aqueous potassium carbonate
6. extractionThe aqueous layer was extracted with chloroform
7. dry with materialdried with anhydrous magnesium sulfate
8. concentrationconcentrated in vacuo
9. additionThe residue was charged on a column of silica gel (C-200, 40 g)
10. washeluted successively with chloroform and chloroformmethanol (20:1)

ORD record

ord-3a35f0d906e34dfcb139126f857df4f2

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04894453