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

HRID 1814314노트

반응식

HRID 1814314 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7ae9f339d610400a9c014147c27df4cb
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06875765B2

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