Benzyl Alcohol → HCID 19711369, compound

HRID 2210066Notes

Reaction equation

HRID 2210066 reaction equation
C([CH:4]([CH3:28])[CH2:5][C:6]1[CH:7]=[C:8]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:9]=[C:10]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=1)(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:36])C=CC=CC=1.C([N:48]([CH2:51]C)CC)C.[CH2:53]([OH:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>O1CCOCC1>[CH2:53]([O:60][C:51]([NH:48][CH:4]([CH3:28])[CH2:5][C:6]1[CH:7]=[C:8]([CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[CH:9]=[C:10]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)[CH:11]=1)=[O:36])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19711377HCID 19711377, compound

Product 1

HCID 19711369HCID 19711369, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of t-butyl 3-[3-(2-carboxy-1-propyl)-5-(3-pyridylmethyl)phenyl]propanoate (Preparation 38; 1.84 g), diphenylphosphoryl azide (1.45 g) and triethylamine (0.53 g) in dry 1,4-dioxane (12 ml) was heated at 100° C. for 45 minutes. Benzyl alcohol (0.78 g) was then added and the resulting solution heated under reflux for 18 hours and then evaporated under vacuum. The residue was chromatographed on silica gel using dichloromethane:methanol (95:5) as eluent, then the product fractions combined and evaporated under vacuum to give the title compound as an oil (2.30 g); Rf 0.25 (SS 1); δ (CDCl3): 1.08(3H,d), 1.40(9H,s), 2.48(2H,t), 2.55-2.63(2H,m), 2.81(2H,t), 2.89(2H,s), 3.89-3.95(1H,m), 5.07(2H,s), 6.82(1H,s), 6.87(2H,s), 7.12-7.18(1H,m), 7.27-7.42(6H,m), 8.40- 8.45(2H,m).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureunder reflux for 18 hours
  3. customevaporated under vacuum
  4. customThe residue was chromatographed on silica gel
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-f7a0bf2500c54c09846f3d7d4a29cd82
Source dataset
uspto-grants-1995_10
Patent number
US05457118

Reaction notes

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