Oxygen → HCID 57634373, compound

HRID 556021Notes

Reaction equation

HRID 556021 reaction equation
O=O.[C:3]([NH:11][C:12](=[CH:17][N:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[C:3]([NH:11][CH:12]([CH2:17][N:18]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]([O:15][CH3:16])=[O:14])(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 977OxygenHCID 66987425HCID 66987425, compound

Product 1

HCID 57634373HCID 57634373, compound

Reagents, catalysts & solvents 1

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)Catalyst

Procedure

With exclusion of oxygen, an autoclave was charged with 1 g (2.68 mmol) of methyl 2-benzoylamino-3-diphenylaminoacrylate and 40 mg (0.042 mmol) of tris(triphenylphosphine)rhodium(I) chloride. After purging with argon, 40 ml of oxygen-free methanol were added. The autoclave was sealed gas-tight and the solution was hydrogenated at RT for 20 hours (h). The autoclave was decompressed and purged with nitrogen. The solvent was evaporated off under reduced pressure and the residue was chromatographed through a column filled with silica gel 60 (eluent: 1:1 ethyl acetate/heptane). After the solvents had been evaporated off under reduced pressure, a white solid remained, which was utilized for the formulation of a method and as a system test for the determination of the enantiomeric purity by HPLC on chiral phase.

Workup

  1. customAfter purging with argon, 40 ml of oxygen-free methanol
  2. additionwere added
  3. customThe autoclave was sealed gas-tight
  4. custompurged with nitrogen
  5. customThe solvent was evaporated off under reduced pressure
  6. customthe residue was chromatographed through a column
  7. additionfilled with silica gel 60 (eluent: 1:1 ethyl acetate/heptane)
  8. customAfter the solvents had been evaporated off under reduced pressure

Sources & evidence

ORD record
ord-c73ad1ef5b75450e91ee0699cb46ab1d
Source dataset
uspto-grants-2011_11
Patent number
US08053590B2

Reaction notes

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