Triphenylphosphine → Ethyl 3-phenyl-3-(6-{3-[(pyridin-2-yl)(2,2,2-trichloroethoxycarbonyl) amino]propoxy}indol-3-yl)propionate

HRID 351927

反応式

HRID 351927 の反応式
[C:1]1([CH:7]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][CH2:25][CH2:26]O)=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:28][C:29]([Cl:42])([Cl:41])[CH2:30][O:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=1)=[O:33].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[C:1]1([CH:7]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([O:23][CH2:24][CH2:25][CH2:26][N:34]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)[C:32]([O:31][CH2:30][C:29]([Cl:28])([Cl:41])[Cl:42])=[O:33])=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 116876422,2,2-Trichloroethyl pyridin-2-ylcarbamateHCID 15549282Ethyl 3-phenyl-3-[6-(3-hydroxypropoxy)indol-3-yl]propionate

生成物 1

HCID 15549283Ethyl 3-phenyl-3-(6-{3-[(pyridin-2-yl)(2,2,2-trichloroethoxycarbonyl) amino]propoxy}indol-3-yl)propionate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

500 mg (1.36 mmol) of 5 and 550 mg (2.04 mmol) of 2-(2,2,2-trichloroethoxycarbonylamino)pyridine and 907 mg (2.72 mmol) of triphenylphosphine (polymer-bound) are introduced into 7.5 ml of anhydrous THF, and a solution of 0.32 ml (2.04 mmol) of azodicarboxylic acid diethyl ester (diethyl azodicarboxylate, DEAD) in 7.5 ml of THF is added dropwise at room temperature over the course of 30 minutes. The TLC check shows complete conversion after 1.5 hours. The polymer is filtered off, and the solution is washed with a little water, dried and evaporated. The residue can be purified by chromatography on silica gel (eluent gradient toluene/acetone 20:1→4:1), giving ethyl 3-phenyl-3-(6-{3-[(pyridin-2-yl)(2,2,2-trichloroethoxycarbonyl)amino]propoxy}indol-3-yl)propionate.

後処理

  1. customafter 1.5 hours
  2. filtrationThe polymer is filtered off
  3. washthe solution is washed with a little water
  4. customdried
  5. customevaporated
  6. customThe residue can be purified by chromatography on silica gel (eluent gradient toluene/acetone 20:1→4:1)

出典と根拠

ORDレコード
ord-6368bd859e1d47f7bc07fce48a640c73
出典データセット
uspto-grants-2004_06
特許番号
US06743810B2

関連ノート

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