Triphenylphosphine → (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HRID 517570ノート

反応式

HRID 517570 の反応式
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].[C:18]([NH:37]CCO)(C1C=CC=CC=1)(C1C=CC=CC=1)[C:19]1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(OCC)(=O)C>[NH2:37][CH2:18][CH2:19][N:11]1[C:10](=[O:15])/[C:9](=[CH:8]/[C:7]2[CH:16]=[CH:17][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)/[S:13][C:12]1=[O:14]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 31256082-((Triphenylmethyl)amino)ethanolHCID 5363146Diisopropyl azodicarboxylateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

生成物 1

HCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione収率 182.5%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Compound 2 (1.26 g, 5.08 mmol), 2-(tritylamino)ethanol (2.00 g, 6.60 mmol) and triphenylphosphine (1.80 g, 6.86 mmol) were dissolved in 51 mL of anhydrous THF, and stirred at room temperature for 5 min. DIAD (1.3 mL, 6.60 mmol) was added to the reaction mixture and then stirred overnight at 45° C. The reaction mixture was diluted with ethyl acetate and washed with sat'd NH4Cl aqueous solution. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (30% ethyl acetate in hexanes) to afford 3 (75.0%, 2.71 g) as a white solid.

後処理

  1. stirringstirred overnight at 45° C
  2. washwashed with sat'd NH4Cl aqueous solution
  3. customThe organic layer was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica column chromatography (30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-857af05a6f5048b286be6d7c0070d824
出典データセット
uspto-grants-2015_08
特許番号
US09115122B2

反応ノート

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