Benzyl Alcohol → HCID 10248693, compound

HRID 2257954Notes

Reaction equation

HRID 2257954 reaction equation
C([C:4]1[C:5](=[O:19])[N:6]([CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]([CH3:10])=[CH:8][CH:9]=1)(O)=O.C([N:22]([CH2:25]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.[CH2:44]([OH:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>O1CCOCC1>[CH2:44]([O:51][C:25]([NH:22][C:4]1[C:5](=[O:19])[N:6]([CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[C:7]([CH3:10])=[CH:8][CH:9]=1)=[O:34])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 19027993HCID 19027993, compound

Product 1

HCID 10248693HCID 10248693, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the compound of Example 92 (13.0 g, 48.7 mmole) suspended in dioxane (150 ml), was added triethylamine (7.7 mL, 55 mmole) dropwise rapidly with stirring followed by diphenylphosphoryl azide (16 mL, 73 mmole). The suspension was heated for 2 h using a preheated 110° C. oil bath. Benzyl alcohol (7.6 g, 73 mmole) was then added and the mixture was stirred at 110° C. for 20 hours. The reaction mixture was cooled and concentrated. The residue was suspended in ethyl acetate (400 mL) and was washed with 3% HCl, then brine, dried over magnesium sulfate and concentrated. The crude product was chromatographed on flash silica gel using 20-67% ethyl acetate/hexanes to afford the title compound (14.2 g, 78% yield) as a white solid. Rf=0.53 (silica gel, 33% ethyl acetate/hexanes).

Workup

  1. temperatureThe suspension was heated for 2 h
  2. customusing a preheated 110° C.
  3. stirringthe mixture was stirred at 110° C. for 20 hours
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated
  6. washwas washed with 3% HCl
  7. dry with materialbrine, dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was chromatographed on flash silica gel using 20-67% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-77fa620671a646daa59d93f4e21d8e98
Source dataset
uspto-grants-1997_08
Patent number
US05658930

Reaction notes

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