Water → HCID 18779235, compound

HRID 1422307Notes

Reaction equation

[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]1[N:25]([S:26](=[O:31])(=[O:30])[N:27]([CH3:29])[CH3:28])[C:24]([Si](C(C)(C)C)(C)C)=[N:23][CH:22]=1.O>CN(C)C=O>[CH3:28][N:27]([CH3:29])[S:26]([N:25]1[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[CH:22][N:23]=[CH:24]1)(=[O:30])=[O:31]

Participants

Conditions

Temperature: 100 °C

Procedure

Potassium phthalimide (1.67 g, 9.00 mmol) was added to a solution of the product from step b (2.10 g, 4.50 mmol) in dry N,N-dimethylformamide (10 ml), under an atmosphere of argon. The mixture was stirred and heated at 100° C. for 18 h and allowed to cool to room temperature. Water (75 ml) was added and the mixture extracted with dichloromethane (3×40 ml). The combined extracts were evaporated, the residue dissolved in ethyl acetate (75 ml) and the solution washed five times with brine. The solvent was evaporated and the residue purified by flash column chromatography (silica; ethyl acetate), from which the product was isolated as a yellow oil (1.75 g, 93%).

Workup

temperatureto cool to room temperature
extractionthe mixture extracted with dichloromethane (3×40 ml)
customThe combined extracts were evaporated
dissolutionthe residue dissolved in ethyl acetate (75 ml)
washthe solution washed five times with brine
customThe solvent was evaporated
customthe residue purified by flash column chromatography (silica; ethyl acetate), from which the product

Sources & evidence

ORD record: ord-8b33c20dbfb14f15968a5761aa0ce4e4
Source dataset: uspto-grants-2000_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06080871

Reaction notes

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