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 mintes. 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 chloroform-methanol (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 chloroform-methanol (20:1)

ORD record

ord-4e971b417ea542abaa709bacc028876d

Source dataset

uspto-grants-1991_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05001237