tert-Butyl bromoacetate → t-Butyl (5-nitro-1-methyl-uracilyl)acetate

Sodium hydride (0.51 g of a 60% dispersion in mineral oil, 13 mmol) was washed with pentane three times (4 mL each). The compound of Example 109 (2.00 g, 12 mmole) was added portionwise. After the addition was complete, the reaction mixture was stirred for 30 minutes under a nitrogen atmosphere. t-Butyl bromoacetate (1.73 g, 12 mmole) was added in one portion, and the solution was stirred for 3 hours. The reaction mixture was diluted with water (200 mL), and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water (3×50 mL), then brine, dried over magnesium sulfate. The solvent was concentrated, hexanes were added and the solvent was removed in vacuo to afford the title compound (1.97 g) in 59% yield. Rf=0.38 (silica gel, 20% ethyl acetate in dichloromethane.

1. washSodium hydride (0.51 g of a 60% dispersion in mineral oil, 13 mmol) was washed with pentane three times (4 mL each)
2. additionAfter the addition
3. stirringthe solution was stirred for 3 hours
4. extractionextracted with ethyl acetate (3×50 mL)
5. washThe combined organic extracts were washed with water (3×50 mL)
6. dry with materialbrine, dried over magnesium sulfate
7. concentrationThe solvent was concentrated
8. additionhexanes were added
9. customthe solvent was removed in vacuo

ORD record

ord-b117741c08764cec9dfd9a311338c8a8

Source dataset

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05656645