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

HRID 2116687노트

반응식

HRID 2116687 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1c5deb9ea85e4555925309a503e43c1b
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439237B2

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