Sodium hydride → HCID 54110240, compound

HRID 2289692Notes

Reaction equation

P(=O)([O-])O[C:3]([CH2:8][CH3:9])([CH2:6][CH3:7])[C:4]#N.[H-].[Na+].C(C1C=C(C(C)C)[C:19]([O:25][S:26](=[O:47])(=[O:46])[NH:27][C:28](=[O:45])[CH2:29][C:30]2[C:35](C(C)C)=[CH:34][C:33]([CH:39]([CH3:41])[CH3:40])=[CH:32][C:31]=2[CH:42]([CH3:44])[CH3:43])=C(C(C)C)C=1)=O>O1CCCC1>[C:28]([CH:29]=[CH:4][C:3]1[CH:8]=[C:9]([CH:30]([CH3:31])[CH3:35])[C:19]([O:25][S:26](=[O:47])(=[O:46])[NH:27][C:28](=[O:45])[CH2:29][C:30]2[C:35]([CH:39]([CH3:41])[CH3:40])=[CH:34][C:33]([CH:39]([CH3:41])[CH3:40])=[CH:32][C:31]=2[CH:42]([CH3:44])[CH3:43])=[C:7]([CH:33]([CH3:34])[CH3:32])[CH:6]=1)#[N:27]

Participants

Conditions

Temperature: -78 °C

Procedure

Diethylcyanomethyl phosphonate (1.49 mL, 9.2 mmol) was added dropwise to a suspension of sodium hydride (0.37 g, 9.2 mmol) in 20 mL tetrahydrofuran at 0° C. After 15 minutes, the reaction was cooled to -78° C. and a solution of [(2,4,6-triisopropyl-phenyl)-acetyl]-sulfamic acid 4-formyl-2,6-diisopropyl-phenyl ester (2.32 g, 4.4 mmol) in 75 mL tetrahydrofuran was added dropwise. The reaction was allowed to warm to room temperature overnight and then concentrated in vacuo and partitioned the residue between 1 M HCl and dichloromethane. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give an oily solid. Chromatography on silica gel (20% ethyl acetate/hexanes) gave 1.16 g of the title compound as a white solid; mp 157-160° C.

Workup

temperatureto warm to room temperature overnight
concentrationconcentrated in vacuo
custompartitioned the residue between 1 M HCl and dichloromethane
dry with materialThe organic layer was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give an oily solid

Sources & evidence

ORD record: ord-2bef5b9eeccd454a9267a1e2782e57c3
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06093744

Reaction notes

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