Triphenylphosphine → 3-(4-Amino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino)-n-methyl-succinamic acid tert-butyl ester

HRID 1814314ノート

反応式

HRID 1814314 の反応式
[N:1]1[C:10]2[C:5](=[C:6]([CH2:11][CH2:12][OH:13])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:33]([O:37][C:38](=[O:57])[CH2:39][CH:40]([NH:45][S:46]([C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][C:50]=1O)(=[O:48])=[O:47])[C:41]([NH:43][CH3:44])=[O:42])([CH3:36])([CH3:35])[CH3:34].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:33]([O:37][C:38](=[O:57])[CH2:39][CH:40]([NH:45][S:46]([C:49]1[CH:54]=[CH:53][C:52]([NH2:55])=[CH:51][C:50]=1[O:13][CH2:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH:4]=[CH:3][CH:2]=[N:1]2)(=[O:48])=[O:47])[C:41]([NH:43][CH3:44])=[O:42])([CH3:36])([CH3:34])[CH3:35]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 225041322-(Quinolin-5-yl)ethan-1-olHCID 696924193-(4-amino-2-hydroxy-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester

生成物 1

HCID 696922433-(4-Amino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino)-n-methyl-succinamic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 0.167 g (0.972 mmol) 2-quinolin-5-yl-ethanol, 0.48 g (1.94 mmol) triphenyl phosphine, and 0.392 g (0.972 mmol) 3-(4-amino-2-hydroxy-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester was stirred in 25 mL THF at room temperature under a nitrogen atmosphere. 0.31 mL (1.94 mmol) diethyl azodicarboxylate was added dropwise and the mixture stirred 18 h. TLC anaylsis indicated complete reaction. The solvent was evaporated under reduced pressure and the residue purified on silica eluting with 1:1 hexanes:EtOAc to EtOAc yielding 0.23 g (43%) of 3-(4-amino-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino)-N-methyl-succinamic acid tert-butyl ester as a colorless foam. MS (APCI) m/z 559 (M+1).

後処理

  1. customTLC anaylsis indicated complete reaction
  2. customThe solvent was evaporated under reduced pressure
  3. customthe residue purified on silica eluting with 1:1 hexanes

出典と根拠

ORDレコード
ord-7ae9f339d610400a9c014147c27df4cb
出典データセット
uspto-grants-2005_04
特許番号
US06875765B2

反応ノート

読み込み中…