Triphenylphosphine → 4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-ethoxy-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 577551노트

반응식

HRID 577551 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH2:34]([O:41][C:42]1[C:47]([CH2:48][N:49]([CH2:63][CH2:64][OH:65])[C:50](=[O:62])[C:51]2[C:56](O)=[CH:55][CH:54]=[C:53]([O:58][CH2:59][CH3:60])[C:52]=2[CH3:61])=[C:46]([CH3:66])[CH:45]=[C:44]([CH3:67])[N:43]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[CH2:34]([O:41][C:42]1[C:47]([CH2:48][N:49]2[C:50](=[O:62])[C:51]3[C:52]([CH3:61])=[C:53]([O:58][CH2:59][CH3:60])[CH:54]=[CH:55][C:56]=3[O:65][CH2:64][CH2:63]2)=[C:46]([CH3:66])[CH:45]=[C:44]([CH3:67])[N:43]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86723778N-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-3-ethoxy-6-hydroxy-N-(2-hydroxyethyl)-2-methylbenzamide

생성물 1

HCID 867237794-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-ethoxy-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one수율 58.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of triphenylphosphine (0.176 g, 0.671 mmol) in THF (5 mL) in an ice bath was treated with diisopropyl azodicarboxylate (0.140 mL, 0.67 mmol) dropwise. After 10 minutes, N-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-3-ethoxy-6-hydroxy-N-(2-hydroxyethyl)-2-methylbenzamide (114e, 0.155 g, 0.334 mmol) was added in one portion. The reaction mixture was stirred in the ice bath overnight and the reaction mixture gradually warmed to room temperature. The reaction mixture was concentrated under vacuum and purified by column chromatography (0-40% ethyl acetate/heptane) to give 4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-ethoxy-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (114f, 0.087 g, 58%) as a clear, thick oil.

후처리

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by column chromatography (0-40% ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-3eed8709e2dc46d0a6f0fafd6daf9e4a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

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