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Triethylamine → Ethyl 4-((S)-(2,4-difluorophenyl)((S)-1,1-dimethylethylsulfinamido)methyl)phenyl(methyl)phosphinate

HRID 1525270
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HRID 1525270 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[NH:9][S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:24][PH:25]([O-])([O-:29])[O:26][CH2:27][CH3:28].CCN(CC)CC>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:23][C:17]1[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=1[C@@H:8]([NH:9][S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[C:5]1[CH:6]=[CH:7][C:2]([P:25]([CH3:24])(=[O:29])[O:26][CH2:27][CH3:28])=[CH:3][CH:4]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 89462687(S)-N-((S)-(4-bromophenyl)(2,4-difluorophenyl)methyl)-2-methylpropane-2-sulfinamide2회HCID 178476778HCID 178476778, 화합물

생성물 1

HCID 89472304Ethyl 4-((S)-(2,4-difluorophenyl)((S)-1,1-dimethylethylsulfinamido)methyl)phenyl(methyl)phosphinate수율 44%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

To (S)—N—((S)-(4-bromophenyl)(2,4-difluorophenyl)methyl)-2-methylpropane-2-sulfinamide, 21-b, (2 g, 5 mmol), ethyl methylphosphite (1.08 g, 10 mmol) and Et3N (1.25 g, 12.5 mmol) in THF (20 ml) was added PdCl2(dppf) (360 mg). The mixture was allowed to stir overnight at reflux. The mixture was filtered and the filtrate was concentrated under vacuum. The residue was taken into ethyl acetate and washed with brine. The organic layer was concentrated under vacuum and the residue was purified over silica gel (dichloromethane:methanol=50/1) to provide the product, 21-c, (950 mg, 44%).

후처리

  1. temperatureat reflux
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated under vacuum
  4. washwashed with brine
  5. concentrationThe organic layer was concentrated under vacuum
  6. customthe residue was purified over silica gel (dichloromethane:methanol=50/1)

출처 및 근거

ORD 기록
ord-87f739a1c35e47b4b1fb5c1ff75b438c
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09079930B2

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