Dimethyl Carbonate → HCID 86637074, compound

HRID 1096872Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]([CH2:11][C:12](=[O:24])[CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:27][O:28][C:29](=O)[O:30]C>C1COCC1.CCOC(C)=O>[CH3:27][O:28][C:29]([CH:11]1[C:12](=[O:24])[CH2:13][CH:14]2[N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:15]2)=[O:30]

Participants

Conditions

Temperature: 0 °C

Procedure

Compound W (15.91 g, 46.7 mmol) was dissolved in THF (100 mL). NaH (55% in oil, 4.71 g, 98 mmol) was added portionwise, followed by dimethylcarbonate (8.86 mL, 105 mmol). The reaction mixture was heated to reflux for 1 h. The mixture was cooled to 0° C. with an ice bath, and treated cautiously with ice-water (50 mL). The org. layer was diluted with EtOAc (200 mL), and washed with aq. 1M HCl (100 mL), and with brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 1:3→1:2→1:1→2:1) yielded the title compound (Rf=0.7, EtOAc/heptane 1:1) as a yellow oil (10.96 g, 58%). LC-MS: tR=1.03, ES+: 399.25.

Workup

temperatureThe reaction mixture was heated
temperatureto reflux for 1 h
washwashed with aq. 1M HCl (100 mL)
dry with materiallayer was dried over MgSO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customPurification of the crude by FC (EtOAc/heptane 1:3→1:2→1:1→2:1)

Sources & evidence

ORD record: ord-60921e02c6554275b8a3c92cc05b7224
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138340B2

Reaction notes

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