Triphenylphosphine → 6-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one

HRID 855724노트

반응식

HRID 855724 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]1([CH2:25][CH2:26][OH:27])[CH:24]=[CH:23][N:22]=[N:21]1.O[C:29]1[CH:38]=[C:37]2[C:32]([C:33](=[O:47])[N:34]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[CH:35]=[N:36]2)=[CH:31][C:30]=1[O:48][CH3:49].N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl>[CH3:49][O:48][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:29]=1[O:27][CH2:26][CH2:25][N:20]1[CH:24]=[CH:23][N:22]=[N:21]1)[N:36]=[CH:35][N:34]([CH2:39][O:40][C:41](=[O:46])[C:42]([CH3:43])([CH3:44])[CH3:45])[C:33]2=[O:47]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-olHCID 10804576(7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

생성물 1

HCID 105971686-Methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one수율 276.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Triphenylphosphine (2.82 g, 10.7 mmol) was added to a solution of 2-(1,2,3-triazol-1-yl)ethanol (609 mg, 5.4 mmol), (J. Antib. 1993, 46, 177), and 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.1 g, 3.6 mmol), (prepared as described for the starting material in Example 7), in methylene chloride (70 ml), diethyl azodicarboxylate (600 μl, 10.7 mmol) was then added. After stirring for 2 hours at ambient temperature, the volatiles were removed by evaporation and the residue was purified by column chromatography eluting with methylene chloride/methanol (98/2) to give 6-methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (4 g, 97%).

후처리

  1. custom(prepared
  2. customthe volatiles were removed by evaporation
  3. customthe residue was purified by column chromatography
  4. washeluting with methylene chloride/methanol (98/2)

출처 및 근거

ORD 기록
ord-2e50cdcb55c7431aac687eab2f62cba5
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262201B1

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