Sodium hydride → HCID 18536195, compound

HRID 412122Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:37]=[CH:38][CH:39]=1)[CH2:31]CS([O-])(=O)=O)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C=O)C>[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:37]=[CH:38][CH:39]=1)[CH2:31][N:16]1[CH2:17][CH2:18][N:13]([C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:12])[CH2:14][C:15]1=[O:19])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (430 mg, 10.8 mmol as 60% dispersion in mineral oil) was triturated with hexanes, then suspended in 5 mL of DMF. After cooling to 0° C., 4-(benzyloxy)carbonyl-2-piperazinone was added (1.68 g, 7.18 mmol). After 15 minutes, a solution of the product from Step H (2.096 g, 7.18 mmol) in 2 mL of DMF was added, followed by a 1 mL DMF rinse. The reaction was warmed to room temperature, stirred for 30 minutes, then poured into EtOAc. The organic layer was washed with water, sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting product was purified by silica gel chromatography (60% EtAOAc/hexane) to produce the titled product as a pale yellow oil.

Workup

washrinse
temperatureThe reaction was warmed to room temperature
additionpoured into EtOAc
washThe organic layer was washed with water, sat. aq. NaHCO3 and brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting product was purified by silica gel chromatography (60% EtAOAc/hexane)

Sources & evidence

ORD record: ord-8c42d4a8c9c24dcca9f18fdccccbf7cb
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562823B1

Reaction notes

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