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

HRID 351927

반응식

HRID 351927 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6368bd859e1d47f7bc07fce48a640c73
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743810B2

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