Isobutanol → HCID 22717702, compound

HRID 1582562Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:18]([CH3:20])[CH3:19])[C:9]([N:11]2[C:15](=[O:16])[NH:14][C:13](=[O:17])[O:12]2)=[O:10])=[CH:4][CH:3]=1.[CH3:21][CH:22]([CH3:25])[CH2:23]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:18]([CH3:20])[CH3:19])[C:9]([N:11]2[C:15](=[O:16])[N:14]([CH2:21][CH:22]([CH3:25])[CH3:23])[C:13](=[O:17])[O:12]2)=[O:10])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A 50 mL round bottom flask equipped with a thermometer, a stirrer, an addition funnel, and a nitrogen inlet was charged with N-(4-fluorophenyl)-N-(1-methylethyl)-3,5-dioxo-1,2,4-oxadiazolidine-2-carboxamide (5.5 g, 0.019 m), 2-methyl-1-propanol (3 g, 0.04 mol), triphenylphosphine (6.3 g, 0.021 mol) and tetrahydrofuran (60 mL). The reaction solution was cooled to 15° C. and diethyl azodicarboxylate (4.2 g, 0.024 mol) in tetrahydrofuran (10 mL) was added dropwise over a period of 10 min. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was flash chromatographed (silica gel, 9:1 hexane-ethyl acetate) to provide the title compound as a white solid (5.6 g, 88%). The solid has a melting range of 80-81° C., and was identical to the material prepared in Example 8, Step B.

Workup

customA 50 mL round bottom flask equipped with a thermometer, a stirrer, an addition funnel, and a nitrogen inlet
customThe solvent was removed under reduced pressure
customchromatographed (silica gel, 9:1 hexane-ethyl acetate)

Sources & evidence

ORD record: ord-93dbdbe7cd134d42a8e251d349cc9b0d
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06737383B1

Reaction notes

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