1-Hydroxybenzotriazole → HCID 67095925, compound

Temperature

0 °C

A mixture of 1,4-dioxa-spiro[4.5]decane-6-carboxylic acid (3.72 g, 20 mmol), N,N-dicyclohexyl-carbodiimid (2.06 g, 22 mmol) and 1-hydroxy-benzotriazole (3.03 g, 22 mmol) in tetrahydrofuran (40 mL) was stirred at 0° C. for 3.5 h. N-Hydroxy-acetamidine (1.48 g, 20 mmol) was added to the mixture and stirring was continued at 20° C. for 18 h. The reaction mixture was cooled to 0° C. and insoluble material was removed by filtration. The filtrate was evaporated under reduced pressure. Toluene (250 mL) was added to the remaining oil and the mixture was heated at reflux for 5 h, water being removed using a Dean-Stark trap. The solution was cooled, solvents were evaporated under reduced pressure, and the residual material was purified by column chromatography on silica gel (100 g) using heptane/20-80% ethyl acetate as eluent to give the title compound (2.70 g, 60%). Obtained as light-yellow oil. MS ISP (m/e): 225.1 [(M+H)+].

1. stirringstirring
2. waitwas continued at 20° C. for 18 h
3. temperatureThe reaction mixture was cooled to 0° C.
4. custominsoluble material was removed by filtration
5. customThe filtrate was evaporated under reduced pressure
6. additionToluene (250 mL) was added to the remaining oil
7. temperaturethe mixture was heated
8. temperatureat reflux for 5 h
9. customwater being removed
10. temperatureThe solution was cooled
11. customsolvents were evaporated under reduced pressure
12. customthe residual material was purified by column chromatography on silica gel (100 g)

ORD record

ord-853c195e336e4a99ac39695dece896bf

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923450B2