Acetic Anhydride → HCID 12946291, compound

HRID 1449380Notes

Reaction equation

[F:1][C:2]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]([OH:8])[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10].C(OC(=O)C)(=O)C.[C:23]1(=[N:27]O)[CH2:26][CH2:25][CH2:24]1>N1C=CC=CC=1.CC(C)=O>[F:1][C:2]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:7]([O:8][N:27]=[C:23]2[CH2:26][CH2:25][CH2:24]2)[NH:6][C:5](=[O:9])[NH:4][C:3]1=[O:10]

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 5-fluoro-6-hydroxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate (6.60 g., 30 mmoles), acetic anhydride (3.27 g., 32 mmoles), pyridine (10 ml.) and acetone (10 ml.) were mixed and allowed to stand overnight at ordinary temperature (18°-23° C.). To this mixture were added cyclobutanone oxime (3.82 g., 45 mmoles) and pyridine (5 ml.) which was heated at 60° C. for 2 hours. Then, volatiles were removed under reduced pressure and the remaining mass was chromatographed on a column of silica gel with chloroform/acetone=85/15(V/V) to give 4.78 g of ethyl 5-fluoro-6-cyclobutylideneaminooxy-1,2,3,4,5,6-hexahydro-2,4-dioxopyrimidine-5-carboxylate.

Workup

customThen, volatiles were removed under reduced pressure
customthe remaining mass was chromatographed on a column of silica gel with chloroform/acetone=85/15(V/V)

Sources & evidence

ORD record: ord-4c10bd5cbd684910a5533f1a769810c4
Source dataset: uspto-grants-1980_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04190656

Reaction notes

Loading…