Triphenylphosphine → HCID 66991113, compound

HRID 454702Notes

Reaction equation

HRID 454702 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.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.[CH2:49]([O:56][C:57]1[CH:81]=[CH:80][C:79](O)=[CH:78][C:58]=1[C:59]([NH:61][C:62]1[CH:71]=[C:70]([C:72]2[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=2)[CH:69]=[CH:68][C:63]=1[C:64]([O:66][CH3:67])=[O:65])=[O:60])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>O1CCCC1>[CH2:49]([O:56][C:57]1[CH:81]=[CH:80][C:79]([O:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)=[CH:78][C:58]=1[C:59]([NH:61][C:62]1[CH:71]=[C:70]([C:72]2[CH:73]=[CH:74][CH:75]=[CH:76][CH:77]=2)[CH:69]=[CH:68][C:63]=1[C:64]([O:66][CH3:67])=[O:65])=[O:60])[C:50]1[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine3×HCID 75555Diisopropyl diazene-1,2-dicarboxylate3×HCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 66990532HCID 66990532, compound

Product 1

HCID 66991113HCID 66991113, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (0.26 g), triphenylphosphine (0.35 g), and diisopropyl azodicarboxylate (0.26 mL) were added to a tetrahydrofuran (5.0 mL) solution of methyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate (0.50 g), followed by stirring at room temperature for 30 minutes. Triphenylphosphine (0.35 g) and diisopropyl azodicarboxylate (0.26 mL) were added to the reaction mixture, followed by stirring at room temperature for 30 minutes. Triphenylphosphine (0.35 g) and diisopropyl azodicarboxylate (0.26 mL) were added to the reaction mixture, followed by stirring at room temperature for 30 minutes. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 95-70% hexane/ethyl acetate] to obtain methyl 2-(2-(benzyloxy)-5-((1-(tert-butoxycarbonyl)piperidin-4-yl)methoxy)benzamido)-4-phenylbenzoate as a yellow oily substance.

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. stirringby stirring at room temperature for 30 minutes
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 95-70% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-a51bc0d51c4d4c5883bb3b23b3f5d6c8
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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