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

HRID 1525259
ノート
印刷プレビュー

反応式

HRID 1525259 の反応式
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][CH:17]=2)[NH:9][S@:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[CH:4][CH:3]=1.[CH3:23][PH:24]([O-])([O-:28])[O:25][CH2:26][CH3:27].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]>[CH3:13][C:12]([CH3:15])([S@@:10]([NH:9][C@@H:8]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:5]1[CH:6]=[CH:7][C:2]([P:24]([CH3:23])(=[O:28])[O:25][CH2:26][CH3:27])=[CH:3][CH:4]=1)=[O:11])[CH3:14]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 89464549(S)-N-((S)-(4-bromophenyl)(4-fluorophenyl)methyl)-2-methylpropane-2 sulfinamide2 回HCID 178476778HCID 178476778、化合物

生成物 1

HCID 89472221Ethyl 4-((S)-((S)-1,1-dimethylethylsulfinamido)(4-fluorophenyl)-methyl)phenyl(methyl)phosphinate収率 68%

試薬・触媒・溶媒 2

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

実験手順

To (S)—N—((S)-(4-bromophenyl)(4-fluorophenyl)methyl)-2-methylpropane-2-sulfinamide, 19-b, (10 g, 0.026 mol), ethyl methylphosphite (5.6 g, 0.052 mol) and Et3N (7.88 g, 0.78 mol) in THF (100 ml) was added PdCl2(dppf) (2.2 g). 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 dichloromethane and washed with brine. The organic layer was concentrated under vacuum and the residue was purified over silica gel (petroleum ether:ethyl acetate=1/1) to provide the product, 19-c, (6.9 g, 68%).

後処理

  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 (petroleum ether:ethyl acetate=1/1)

出典と根拠

ORDレコード
ord-d937aa2981a3418ea0c9f30e7efbbc17
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09079930B2

反応ノート

読み込み中…

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