Bromotrimethylsilane → HCID 16110080, compound

Bromotrimethylsilane (4.7 ml, 35 mmol) was added to a solution of 9 (1.34 g, 3.13 mmol) in acetonitrile (30 ml) and the mixture was set aside at ambient temperature for 20 h. The mixture was evaporated at 30° C., the residue coevaporated with acetonitrile (2×30 ml) and 90% aqueous methanol (50 ml) was added. The solution was neutralized with 1 M triethylammonium hydrogencarbonate to pH 7 and evaporated. The residue was partitioned between water (100 ml) and ether (100 ml), an aqueous layer evaporated to a volume 5 ml and applied onto a column of Dowex 1 (AcO− form, 100 ml). Elution was performed with water (500 ml), then with a linear gradient of acetic acid (0.1-1 M, 1.5 l) and finally, the product was eluted with 1 M formic acid. UV absorbing fractions were taken down in vacuo and the residue coevaporated with water (4×20 ml). The residue was crystallized from water. Yield 350 mg (37%) of compound 3, identical with the product described in Example 1. M.p. 175-178° C.,

1. customThe mixture was evaporated at 30° C.
2. additionwas added
3. customevaporated
4. customThe residue was partitioned between water (100 ml) and ether (100 ml)
5. customan aqueous layer evaporated to a volume 5 ml
6. washElution
7. washwith a linear gradient of acetic acid (0.1-1 M, 1.5 l) and finally, the product was eluted with 1 M formic acid
8. customUV absorbing fractions
9. customThe residue was crystallized from water

ORD record

ord-a3c87e223fb54f539a7811abc32e2c94

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153787B2