Acetate → HCID 44223459, compound

HRID 1021201Notes

Reaction equation

C[O:2][C:3]1[C:8]([CH3:9])=[C:7]([CH3:10])[C:6]([O:11]C)=[C:5]([CH3:13])[C:4]=1[CH2:14][CH2:15][CH2:16][C:17]([NH:19][CH2:20][CH2:21][OH:22])=[O:18].CC#N.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C([O-])(=O)C>O>[OH:22][CH2:21][CH2:20][NH:19][C:17](=[O:18])[CH2:16][CH2:15][CH2:14][C:4]1[C:3](=[O:2])[C:8]([CH3:9])=[C:7]([CH3:10])[C:6](=[O:11])[C:5]=1[CH3:13]

Participants

Conditions

Temperature: 0 °C

Procedure

Crude 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-N-(2-hydroxyethyl)butanamide (1.105 g, 3.57 mmol) was taken up into 40 mL MeCN and 2 mL H2O and cooled to 0° C. To this was added CAN (4.35 g, 7.86 mmol, 2.2 equiv) in 5 mL H2O dropwise over 5 minutes. The reaction was stirred for 0.25 h until judged complete by HPLC and 50 mL ipropyl acetate was added. The organic layer was washed 4×5 mL saturated aqueous NaCl, dried over aqueous Na2SO4 and concentrated to a yellow powder. Flash chromatography (gradient elution 80-100% EtOAc/heptane) yielded 619 mg of N-(2-hydroxyethyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow powder. M++H=280 m/z; 1H NMR (400 MHz, CDCl3) δ=6.38 (s, 1 H), 3.77 (t, 2 H), 3.47 (m, 2 H), 2.54 (t, 2 H), 2.29 (t, 2 H), 2.05 (s, 3 H), 2.01 (s, 6 H), 1.76 (m, 2 H+H2O) ppm.

Workup

additionwas added
washThe organic layer was washed 4×5 mL saturated aqueous NaCl
dry with materialdried over aqueous Na2SO4
concentrationconcentrated to a yellow powder
washFlash chromatography (gradient elution 80-100% EtOAc/heptane)

Sources & evidence

ORD record: ord-1a242927d90f4d11abb9e17ec9960cf7
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716527B2

Reaction notes

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