Dimethyl Sulfoxide → HCID 131725289, compound

HRID 891195Notes

Reaction equation

HRID 891195 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH2:4][N:5]([C:18](=[O:31])[CH:19]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20]C=C)[CH2:6][C:7]([C:9]([CH3:17])([CH3:16])[O:10][SiH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH2:8].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:32])[CH2:4][N:5]1[CH2:6][C:7]([C:9]([CH3:16])([CH3:17])[O:10][SiH2:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:8][CH2:20][CH:19]([NH:23][C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])[C:18]1=[O:31]

Participants

5

Reactant 2

HCID 679Dimethyl SulfoxideHCID 131725290HCID 131725290, compound

Product 1

HCID 131725289HCID 131725289, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178479819HCID 178479819, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Super Grubbs catalyst (2 g) is added to a solution {(2-tert-butoxycarbonylamino-pent-4-enoyl)-[2-(tert-butyl-dimethyl-silanyloxymethyl)-allyl]-amino}-acetic acid methyl ester, 16, (4.1 g, 8.7 mmol) in CH2Cl2(100 mL). The solution is refluxed for 1 hour then DMSO (10 mL) is added and stirring is continued for another 12 hours at room temperature. The solvent is removed in vacuo and the residue purified over silica (EtOAc/hexane) to afford 3.7 g (96% yield) of the desired product. 1H NMR (CDCl3) δ 5.80–5.78 (d, J=6.3 Hz, 1H), 5.65 (bs, 1H), 5.03–4.96 (m, 1H), 4.56–4.48 (m, 2H), 3.98 (s, 2H), 3.98–3.92 (d, J=17.4 Hz, 1H), 3.73 (s, 3H), 3.44–3.38 (d, J=17.7, 1H), 2.74–2.67 (d, d, J=18, 3.3 Hz, 1H), 2.30–2.18 (m, 1H), 1.45 (s, 9H), 0.89 (s, 9H), 0.06 (s, 6H); 13C (CDCl3) δ 172.9, 169.6, 155.2, 135.6, 124.6, 79.7, 66.9, 60.5, 52.4, 50.0, 49.8, 47.6, 33.1, 28.5, 26.0, 18.4,14.4, −5.0; MS 442 (M+H)+.

Workup

  1. temperatureThe solution is refluxed for 1 hour
  2. customThe solvent is removed in vacuo
  3. customthe residue purified over silica (EtOAc/hexane)

Sources & evidence

ORD record
ord-676e3ed7d6f14241bb0256db72d3b1d6
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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