Triphenylphosphine → HCID 58508535, compound

HRID 454628Notes

Reaction equation

HRID 454628 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].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.[OH:48][C:49]1[CH:73]=[C:72](O)[CH:71]=[CH:70][C:50]=1[C:51]([NH:53][C:54]1[CH:63]=[C:62]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH:61]=[CH:60][C:55]=1[C:56]([O:58][CH3:59])=[O:57])=[O:52]>O1CCCC1>[OH:48][C:49]1[CH:73]=[C:72]([CH:71]=[CH:70][C:50]=1[C:51](=[O:52])[NH:53][C:54]1[CH:63]=[C:62]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)[CH:61]=[CH:60][C:55]=1[C:56]([O:58][CH3:59])=[O:57])[O:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 75555Diisopropyl diazene-1,2-dicarboxylate2×HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate2×HCID 58508682HCID 58508682, compound

Product 1

HCID 58508535HCID 58508535, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(tert-Butoxycarbonyl)-4-hydroxypiperidine (0.15 g), triphenylphosphine (0.21 g), and diisopropyl azodicarboxylate (0.16 mL) were added to a tetrahydrofuran (3.6 mL) suspension of methyl 2-(2,4-dihydroxybenzamido)-4-phenylbenzoate (0.24 g), followed by stirring at room temperature for 1 hour. 1-(tert-Butoxycarbonyl)-4-hydroxypiperidine (0.066 g), triphenylphosphine (0.086 g), and diisopropyl azodicarboxylate (0.064 mL) were added to the reaction mixture, followed by stirring at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography [eluent: 100-75% hexane/ethyl acetate] to obtain 0.050 g of tert-butyl 4-(3-hydroxy-4-(2-(methoxycarbonyl)-5-phenylphenylcarbamoyl)phenoxy)piperidine-1-carboxylate as a white solid.

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. customThe solvent was evaporated under reduced pressure
  3. customthe obtained residue was purified by silica gel column chromatography [eluent: 100-75% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-bc500e0c86ba4372abb17f70a64db124
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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