Triphenylphosphine → HCID 59497231, 화합물

HRID 1747472노트

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HRID 1747472 반응식
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH2:18]O)[CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][O:21][C:22](=[O:35])[CH2:23][CH2:24][N:25]1[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=2[NH:27][C:26]1=[O:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([CH2:18][N:27]3[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[N:25]([CH2:24][CH2:23][C:22]([O:21][CH3:20])=[O:35])[C:26]3=[O:34])[CH:13]=[C:14]([Cl:17])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 594973521,1-Dimethylethyl 6-chloro-4-(hydroxymethyl)-1H-indole-1-carboxylateHCID 59497358HCID 59497358, 화합물

생성물 1

HCID 59497231HCID 59497231, 화합물수율 47%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

6-Chloro-4-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester 350 mg, 1.24 mmol and 3-(2-Oxo-2,3-dihydro-benzimidazol-1-yl)-propionic acid methyl ester (300 mg 1.36 mmol, from Example 2) are dissolved in tetrahydrofuran 6.0 mL and triphenylphospine (630 mg 1.37 mmol) is added in one portion to the reaction. The reaction is cooled to 0° C. and then diisopropyl azodicarboxylate (265 μL 1.37 mmol) is added drop wise to the reaction over 5 minutes, and warmed to room temperature. The reaction is stirred for 15 minutes and then evaporated in vacuo, and purified on silica gel with hexanes ethyl acetate as the eluent to give the title compound (280 mg, 0.58 mmol, 47%). LCMS (ESMS): m/z 484.9 (M+H+).

후처리

  1. customwise to the reaction over 5 minutes
  2. temperaturewarmed to room temperature
  3. customevaporated in vacuo
  4. custompurified on silica gel with hexanes ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-3f5699ac2e42457589dbc6001c9c3179
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150556B2

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