Triphenylphosphine → HCID 59497231、化合物

HRID 1747472ノート

反応式

HRID 1747472 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 59497231HCID 59497231、化合物収率 47%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-3f5699ac2e42457589dbc6001c9c3179
出典データセット
uspto-grants-2015_10
特許番号
US09150556B2

反応ノート

読み込み中…