1,3-Bis(diphenylphosphino)propane → Methyl 2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-propionate

HRID 2116687Notes

Reaction equation

HRID 2116687 reaction equation
[C:1]([NH:4]/[C:5](=[CH:10]/[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH2:18])=[C:13]([Cl:19])[CH:12]=1)/[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1CC=CCCC=C1.C1CC=CCCC=C1.[Cl-].[Cl-].[Rh].[Rh]>[C:1]([NH:4][CH:5]([CH2:10][C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([NH2:18])=[C:13]([Cl:19])[CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 812191,3-Bis(diphenylphosphino)propaneHCID 69363659methyl (E)-2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-acrylate

Product 1

HCID 69196550Methyl 2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-propionate

Reagents, catalysts & solvents 1

HCID 6436379Rhodium, di-mu-chlorobis((1,2,5,6-eta)-1,5-cyclooctadiene)di-Catalyst

Procedure

20.6 g (73.0 mmol) methyl (E)-2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-acrylate, 0.445 g (0.90 mmol) bis(1,5-cyclooctadiene)-di-rhodium(I)-dichloride, 0.744 g (1.8 mmol) 1,3-bis(diphenylphosphino)-propane were dissolved in 400 ml degassed methanol and 12 ml degassed triethylamine and then hydrogenated at ambient temperature under 3 bar hydrogen pressure. The reaction mixture was evaporated down under reduced pressure and taken up in ethyl acetate. The insoluble precipitate was removed by suction filtering and the filtrate was evaporated down under reduced pressure. The residue was purified by column chromatography.

Workup

  1. customdegassed methanol and 12 ml
  2. customdegassed triethylamine
  3. customhydrogenated at ambient temperature under 3 bar hydrogen pressure
  4. customThe reaction mixture was evaporated down under reduced pressure
  5. customThe insoluble precipitate was removed by suction
  6. filtrationfiltering
  7. customthe filtrate was evaporated down under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1c5deb9ea85e4555925309a503e43c1b
Source dataset
uspto-grants-2008_10
Patent number
US07439237B2

Reaction notes

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