Triphenylphosphine → HCID 86592857, compound

HRID 351253Notes

Reaction equation

HRID 351253 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][O:14][C:15]1[CH:19]=[C:18]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)[N:17]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[N:16]=1.O[CH2:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:13][O:14][C:15]1[CH:19]=[C:18]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH2:36][CH2:37][NH:38][C:39](=[O:45])[O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[CH:24][CH:25]=2)[N:17]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[N:16]=1

Participants

6

Reactant 4

HCID 11776Triphenylphosphine2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 135737360HCID 135737360, compound

Product 1

HCID 86592857HCID 86592857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (0.17 ml) was added dropwise to a suspension of 3-methoxy-1-(4-methoxyphenyl)-5-(4-hydroxyphenyl)-1H-pyrazole (215.6 mg), tert-butyl N-(2-hydroxyethyl)carbamate (352 mg), and triphenylphosphine (286 mg) in THF (3 ml). The mixture was stirred at ambient temperature for 7 hours. Triphenylphosphine (19.1 mg) and diethyl azodicarboxylate (11.5 μl) were added and the mixture stirred at ambient temperature overnight. The mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography eluted with AcOEt/n-hexane=30% to give tert-butyl (2-{4-[3-methoxy-1-(4-methoxyphenyl)-1H-pyrazol-5-yl]phenoxy}ethyl)carbamate

Workup

  1. stirringthe mixture stirred at ambient temperature overnight
  2. concentrationThe mixture was concentrated in vacuo
  3. customThe residue was purified by silica gel column chromatography
  4. washeluted with AcOEt/n-hexane=30%

Sources & evidence

ORD record
ord-49dc18018e6c419e86ec28a9e115d1af
Source dataset
uspto-grants-2007_02
Patent number
US07183306B2

Reaction notes

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