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Triphenylphosphine → 3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester

HRID 1814297
ノート
印刷プレビュー

反応式

HRID 1814297 の反応式
[C:1]([O:5][C:6](=[O:30])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][C:20]=1[OH:29])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].[N:31]1[C:40]2[C:35](=[C:36]([CH2:41][CH2:42]O)[CH:37]=[CH:38][CH:39]=2)[CH:34]=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([O:5][C:6](=[O:30])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26](=[O:28])[CH3:27])=[CH:21][C:20]=1[O:29][CH2:42][CH2:41][C:36]1[CH:37]=[CH:38][CH:39]=[C:40]2[C:35]=1[CH:34]=[CH:33][CH:32]=[N:31]2)(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:2])[CH3:3]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 865882053-(4-acetylamino-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

生成物 1

HCID 865882063-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester
収率 83.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-(4-Acetylamino-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester (0.40 g, 0.9 mmol) was combined with 2-Quinolin-5-yl-ethanol (0.155 g, 0.9 mmol) and triphenyl phosphine (355 mg, 1.3 mmol) in 15 mL THF. The solution was cooled to 0° C. DEAD (0.21 mL, 1.3 mmol) was added. The reaction was slowly warmed to room temperature, and stirred overnight. The reaction mixture was concentrated in vacuo. The crude product was chromatorgraphed using 1:1 ethyl acetate/hexanes followed by ethyl acetate, and then 10% methanol in ethyl acetate to yield 3-[4-acetylamino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester 450 mg (83%) of an off-white solid. MS (APCI) m/z 601.2 (M+1).

後処理

  1. temperatureThe reaction was slowly warmed to room temperature
  2. concentrationThe reaction mixture was concentrated in vacuo

出典と根拠

ORDレコード
ord-52e8ae22065142348375f4dbe1377f90
出典データセット
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06875765B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート