Ethyl Acetate → HCID 10381871, compound

HRID 1755632Notes

Reaction equation

HRID 1755632 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].[C:7]([N:11]1[C:17](=[O:18])[C:16]2[CH:19]=[C:20](I)[CH:21]=[CH:22][C:15]=2[NH:14][C:13](=[O:24])[CH2:12]1)([CH3:10])([CH3:9])[CH3:8].C(OCC)(=O)C>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:7]([N:11]1[C:17](=[O:18])[C:16]2[CH:19]=[C:20]([C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH:21]=[CH:22][C:15]=2[NH:14][C:13](=[O:24])[CH2:12]1)([CH3:10])([CH3:8])[CH3:9]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 10383744HCID 10383744, compound

Product 1

HCID 10381871HCID 10381871, compoundYield 57.8%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

(Trimethylsilyl)acetylene (1.18 mL, 8.4 mmol), copper(I) iodide (0.05 g, 0.28 mmol) and bis(triphenylphosphine)palladium(II) chloride (0.1 g, 0.14 mmol) are added sequentially to a degassed suspension of 4-tert-butyl-3,4-dihydro-7-iodo-1H-1,4-benzodiazepine-2,5-dione (2.5 g, 7.0 mmol) in triethylamine. The reaction mixture is stirred at room temperature for 5 hours and filtered. The filtrate is diluted with ether and concentrated in vacuo to obtain a solid. Chromatography of the solid using silica gel and 15% to 20% ethyl acetate in hexanes solutions gives the title product as a light brown solid (1.33 g, mp 243°-244° C.).

Workup

  1. filtrationfiltered
  2. additionThe filtrate is diluted with ether
  3. concentrationconcentrated in vacuo
  4. customto obtain a solid

Sources & evidence

ORD record
ord-906b21267dff492389ac9170c4878b6e
Source dataset
uspto-grants-1995_08
Patent number
US05438035

Reaction notes

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