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

HRID 1814332
ノート
印刷プレビュー

反応式

HRID 1814332 の反応式
[C:1]([O:5][C:6](=[O:29])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=1[OH:28])(=[O:18])=[O:17])[C:9]([N:11]([O:13][CH3:14])[CH3:12])=[O:10])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:49]1[C:58]2[C:53](=[C:54]([CH2:59][CH2:60]O)[CH:55]=[CH:56][CH:57]=2)[CH:52]=[CH:51][CH:50]=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:29])[CH2:7][CH:8]([NH:15][S:16]([C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[NH2:26])=[CH:21][C:20]=1[O:28][CH2:60][CH2:59][C:54]1[CH:55]=[CH:56][CH:57]=[C:58]2[C:53]=1[CH:52]=[CH:51][CH:50]=[N:49]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 220568ethyl N-ethoxycarbonyliminocarbamateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 865882283-(4-carbamoyl-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester

生成物 1

HCID 865882273-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester
収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a methylene chloride solution of 3-(4-carbamoyl-2-hydroxy-benzenesulfonylamino)-N-methoxy-N-methyl-succinamic acid tert-butyl ester at room temperature was added triphenylphosphine (0.25 g, 0.95 mmol), 2-quinolin-5-yl-ethanol (0.11 g, 0.66 mmol) and diethyl azodicarboxylate (0.17 ml, 1.12 mmol). The reaction was stirred at room temperature for 3 days. The reaction was then concentrated under reduced pressure. The crude residue was chromatographed [silica gel with a gradient of 100% ethyl acetate to 10% (1:9 NH4OH/ethanol) in ethyl acetate] to give 3-[4-carbamoyl-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-N-methoxy-N-methyl-succinamic acid tert-butyl ester as a white foam (0.27 g, 69%). 1H NMR(300 MHz, DMSO) 8.90 (d, 1H), 8.73 (d, 1H), 8.08 (s, 1H), 7.93 (d, 1H), 7.62 (m, 8H), 4.43 (m, 3H), 3.71 (m, 2H), 3.47 (bs, 3H), 2.77 (bs, 3H), 2.54 (dd, 1H), 2.34 (dd, 1H), 1.31 (s, 9H). MS(APCI) m/z 585.1 (M−H), 587.1 (M+1).

後処理

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. customThe crude residue was chromatographed [silica gel with a gradient of 100% ethyl acetate to 10% (1:9 NH4OH/ethanol) in ethyl acetate]

出典と根拠

ORDレコード
ord-f2ccde94e3894e6ea47587d8ceec14d7
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

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