Triethylamine → HCID 88064403, compound

250 mg (0.66 mmol) of the compound from Example 24A and 92 mg (1.32 mmol) of hydroxylamine hydrochloride were suspended in 3.3 ml of ethanol, and the mixture was heated to the boil. 193 μl (1.39 mmol) of triethylamine were added to the hot solution and heating under reflux was continued for a further 1 h. On cooling of the reaction, a colorless solid crystallized out; this solid was filtered off and washed with a little ethanol. This gave 174 mg (69% of theory) of the target compound as a colorless solid. The mother liquor was concentrated under reduced pressure on a rotary evaporator, and the residue was partitioned between water and ethyl acetate. The organic phase was washed successively with 10 ml of water and 10 ml of saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. This gave a further 69 mg (24% of theory) of the target compound in a purity of 87% as a slightly yellowish solid.

1. temperaturethe mixture was heated to the boil
2. temperatureheating
3. temperatureunder reflux
4. temperatureOn cooling of the reaction
5. customa colorless solid crystallized out
6. filtrationthis solid was filtered off
7. washwashed with a little ethanol
8. concentrationThe mother liquor was concentrated under reduced pressure on a rotary evaporator
9. customthe residue was partitioned between water and ethyl acetate
10. washThe organic phase was washed successively with 10 ml of water and 10 ml of saturated sodium chloride solution
11. dry with materialdried over sodium sulfate
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. customThis gave a further 69 mg (24% of theory) of the target compound in a purity of 87% as a slightly yellowish solid

ORD record

ord-e00f174c31934ff7994ed5103611d497

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187466B2