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

HRID 577551ノート

反応式

HRID 577551 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-3eed8709e2dc46d0a6f0fafd6daf9e4a
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

反応ノート

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