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2-(Dimethylamino)ethanol → Methyl[{[4-(2-butynyloxy)phenyl]-sulfonyl}(methyl)amino]{4-[2-(dimethylamino)ethoxy]phenyl}acetate

HRID 2084898
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HRID 2084898 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][OH:24].[CH2:26]([O:30][C:31]1[CH:36]=[CH:35][C:34]([S:37]([N:40]([CH:42]([C:47]2[CH:52]=[CH:51][C:50](O)=[CH:49][CH:48]=2)[C:43]([O:45][CH3:46])=[O:44])[CH3:41])(=[O:39])=[O:38])=[CH:33][CH:32]=1)[C:27]#[C:28][CH3:29].N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:46][O:45][C:43](=[O:44])[CH:42]([N:40]([S:37]([C:34]1[CH:35]=[CH:36][C:31]([O:30][CH2:26][C:27]#[C:28][CH3:29])=[CH:32][CH:33]=1)(=[O:38])=[O:39])[CH3:41])[C:47]1[CH:52]=[CH:51][C:50]([O:24][CH2:23][CH2:22][N:21]([CH3:25])[CH3:20])=[CH:49][CH:48]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86587121Methyl [{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino](4-hydroxyphenyl)acetate

생성물 1

HCID 131722538Methyl[{[4-(2-butynyloxy)phenyl]-sulfonyl}(methyl)amino]{4-[2-(dimethylamino)ethoxy]phenyl}acetate수율 52.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 0.390 g (1.489 mmol) of triphenylphosphine in 8 mL of THF was added 0.150 mL (1.489 mmol) of N,N-dimethylethanolamine followed by 0.400 g (0.993 mmol) of methyl [{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino](4-hydroxyphenyl)acetate (from Example 179) and 0.234 mL (1.489 mmol) of diethyl azodicarboxylate. The reaction was stirred overnight at room temperature and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to give 0.246 g of methyl[{[4-(2-butynyloxy)phenyl]sulfonyl}(methyl)amino]{4-[2-(dimethylamino)ethoxy]phenyl}acetate as a white solid. Electrospray Mass Spec 475.2 (M+H)+.

후처리

  1. concentrationconcentrated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

출처 및 근거

ORD 기록
ord-c085566b619a4875ab0dd029865b7bee
출처 데이터셋
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06716833B2

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