Triphenylphosphine → Tert-butyl 2-(2-(benzyloxy)-5-((1-methylpiperidin-4-yl)oxy)benzamido)-4-phenylbenzoate

HRID 454621Notes

Reaction equation

HRID 454621 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]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.[CH2:42]([O:49][C:50]1[CH:77]=[CH:76][C:75](O)=[CH:74][C:51]=1[C:52]([NH:54][C:55]1[CH:67]=[C:66]([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[CH:65]=[CH:64][C:56]=1[C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])=[O:53])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>O1CCCC1>[CH2:42]([O:49][C:50]1[CH:77]=[CH:76][C:75]([O:1][CH:2]2[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]2)=[CH:74][C:51]=1[C:52]([NH:54][C:55]1[CH:67]=[C:66]([C:68]2[CH:73]=[CH:72][CH:71]=[CH:70][CH:69]=2)[CH:65]=[CH:64][C:56]=1[C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])=[O:53])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 66990772Tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate

Product 1

HCID 66991124Tert-butyl 2-(2-(benzyloxy)-5-((1-methylpiperidin-4-yl)oxy)benzamido)-4-phenylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Hydroxy-1-methylpiperidine (0.17 g), triphenylphosphine (0.39 g), and diisopropyl azodicarboxylate (0.30 mL) were added to a tetrahydrofuran (3.0 mL) solution of tert-butyl 2-(2-(benzyloxy)-5-hydroxybenzamido)-4-phenylbenzoate (0.15 g), followed by stirring at room temperature for 3 hours and 20 minutes. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [eluent: 60-50% hexane/ethyl acetate to 100-90% chloroform/methanol] to obtain tert-butyl 2-(2-(benzyloxy)-5-((1-methylpiperidin-4-yl)oxy)benzamido)-4-phenylbenzoate.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography [eluent: 60-50% hexane/ethyl acetate to 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-526ed0b2263741848e819851c2a9134c
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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