Dimethyl Sulfoxide → Methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,3,4,7-tetrahydro-2-oxo-1H-azepine-1-acetate

HRID 891187Notes

Reaction equation

HRID 891187 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][N:5]([CH2:20][CH:21]=[CH2:22])[C:6](=[O:19])[CH:7]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]C=C.CS(C)=O>Cl[Ru](=CC1C=CC=CC=1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)([P](C1CCCCC1)(C1CCCCC1)C1CCCCC1)Cl.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:23])[CH2:4][N:5]1[CH2:20][CH:21]=[CH:22][CH2:8][CH:7]([NH:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[C:6]1=[O:19]

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 15235394HCID 15235394, compound

Product 1

HCID 15235395Methyl 3-[[(1,1-dimethylethoxy)carbonyl]amino]-2,3,4,7-tetrahydro-2-oxo-1H-azepine-1-acetate

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Grubbs catalyst (0.3 g) is added to a solution of [allyl-(2-tert-butoxycarbonylamino-pent-4-enoyl)amino]acetic acid methyl ester, 1, (0.815 g, 2.5 mmol) in 50 mL of CH2Cl2. The solution is refluxed for 12 hours after which additional catalyst (0.29 g) is added and the solution is refluxed for another 3 hours. The solution is then cooled, 1 mL of DMSO is added, and stirring continued at room temperature for an additional 12 hours. The solvent is removed in vacuo and the residue purified over silica gel to afford the desired product.

Workup

  1. additionis added
  2. temperaturethe solution is refluxed for another 3 hours
  3. temperatureThe solution is then cooled
  4. customThe solvent is removed in vacuo
  5. customthe residue purified over silica gel

Sources & evidence

ORD record
ord-c3dc963ba7df4258ae27712ca1f1dc41
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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