Potassium Carbonate → HCID 118092995, compound

HRID 708896Notes

Reaction equation

[F:1][C:2]1[C:3]([OH:24])=[C:4]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[CH2:5][N:6]([CH3:17])[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH:25]12[O:30][CH:29]1[CH2:28][O:27][CH2:26]2.C([O-])([O-])=O.[K+].[K+]>C(#N)C.O>[F:1][C:2]1[C:3]([O:24][C@H:29]2[C@H:25]([OH:30])[CH2:26][O:27][CH2:28]2)=[C:4]([CH:18]=[C:19]([N+:21]([O-:23])=[O:22])[CH:20]=1)[CH2:5][N:6]([CH3:17])[C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 100 °C

Procedure

27B (680 mg, 2.034 mmol) was mixed with 3,6-dioxabicyclo[3.1.0]hexane (876 mg, 10.17 mmol), and K2CO3 (1546 mg, 11.19 mmol) in acetonitrile (1 mL) and H2O (1 mL) in a sealed tube. The mixture was stirred at 100° C. for 20 h. The reaction was quenched with H2O then extracted with EtOAc (2×) and concentrated. The residue was purified by flash column chromatography (0-90% EtOAc/hexanes) to give a mixture of diastereomers as yellow oil. The diastereomers were further separated by a prep chiral HPLC equipped with a OJ Column to give the first peak 27C (181 mg, 0.431 mmol, 21.17% yield). The relative stereochemistry of hydroxyether is trans however absolute stereochemistry is undetermined MS (ESI) m/z: 421.2 (M+H)+.

Workup

customThe reaction was quenched with H2O
extractionthen extracted with EtOAc (2×)
concentrationconcentrated
customThe residue was purified by flash column chromatography (0-90% EtOAc/hexanes)
customto give
additiona mixture of diastereomers as yellow oil
customThe diastereomers were further separated by a prep chiral HPLC
customequipped with a OJ Column

Sources & evidence

ORD record: ord-cc1a384bee2b47bba11d15b1e0e52cf4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174974B2

Reaction notes

Loading…