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

HRID 577551Notes

Reaction equation

HRID 577551 reaction equation
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

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-3eed8709e2dc46d0a6f0fafd6daf9e4a
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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