Acetic Acid → HCID 90284582, compound

HRID 336342Notes

Reaction equation

F[C:2]1[C:20]([CH:21]=O)=[CH:19][C:5]2[C:6]([N:9]3[C@@H:13](COC)[C@@H:12](C)[O:11][C:10]3=[O:18])=[N:7][O:8][C:4]=2[C:3]=1[F:23].[NH:24]1[C:29](=[O:30])[CH2:28][C:27](=[O:31])[NH:26][C:25]1=[O:32].[C:33]([OH:36])(=O)[CH3:34]>O>[F:23][C:3]1[C:4]2[O:8][N:7]=[C:6]([N:9]3[CH2:13][CH2:12][O:11][C:10]3=[O:18])[C:5]=2[CH:19]=[C:20]2[C:2]=1[N:9]1[CH2:10][C@@H:33]([CH3:34])[O:36][C@@H:5]([CH3:4])[C@@H:6]1[C:28]1([C:27](=[O:31])[NH:26][C:25](=[O:32])[NH:24][C:29]1=[O:30])[CH2:21]2

Participants

Conditions

Temperature: 110 °C

Procedure

Intermediate 6 (800 mg, 1.95 mmol) and pyrimidine-2,4,6(1H,3H,5H)-trione (250 mg, 1.95 mmol) in a mixture of acetic acid (8 mL) and water (2 mL) was heated at 110° C. for 3.5 hours. The solvent was removed and the reaction mixture was purified using Super Critical Fluid Chromatography (Chiralpak IA column with 40% isopropanol and 60% CO2 mobile phase) to give the title compound (571 mg, 61.7% yield) as a solid as the first eluting compound. 1H NMR (300 MHz, DMSO-d6) δ 0.9 (d, 3H) 1.1 (d, 3H) 2.8-3.2 (m, 2H) 7.7 (s, 1H) 11.4 (s, 1H) 11.8 (s, 1H). MS (ES) MH+: 474 for C21H20FN5O7.

Workup

customThe solvent was removed
customthe reaction mixture was purified

Sources & evidence

ORD record: ord-3f180362beac44bc8c52b209fda5c911
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889671B2

Reaction notes

Loading…