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

HRID 2116687ノート

反応式

HRID 2116687 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1c5deb9ea85e4555925309a503e43c1b
出典データセット
uspto-grants-2008_10
特許番号
US07439237B2

反応ノート

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