HCID 11150422, compound → HCID 11196278, compound

HRID 982654Notes

Reaction equation

HRID 982654 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[C@@H:10]([CH3:20])[N:11]([C:16](=[O:19])[CH:17]=[CH2:18])[O:12][CH2:13]C=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:21])[C@H:10]([N:11]1[C:16](=[O:19])[CH:17]=[CH:18][CH2:13][O:12]1)[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 11150422HCID 11150422, compound

Product 1

HCID 11196278HCID 11196278, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of(R)-N-acryloyl-N-allyloxyalanine benzyl ester (6a) (7.32 g, 25.3 mmol) and bis(tricyclohexylphosphine)benzylidene ruthenium dichloride (Grubb's catalyst) (1.04 g, 1.26 mmol, 5 mol %) in dry CH2Cl2 (250 mL) was refluxed with Silica Gel 60H (for TLC) followed by washing with CH2Cl2 (50 mL). After removal of the solvent, the dark oily residue was purified by dry flash chromatography (Silica Gel 60H for TLC, 5% EtOAc-hexanes→15% EtOAc-hexanes) to afford 6.05 g (92%) the olefin 7a identical to that described above.

Workup

  1. washby washing with CH2Cl2 (50 mL)
  2. customAfter removal of the solvent
  3. customthe dark oily residue was purified
  4. dry with materialby dry flash chromatography (Silica Gel 60H for TLC, 5% EtOAc-hexanes→15% EtOAc-hexanes)

Sources & evidence

ORD record
ord-99ef4cdaaaf64c25ac7dd4db213e85f4
Source dataset
uspto-grants-2005_03
Patent number
US06861416B2

Reaction notes

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