Benzyl Alcohol → HCID 18926524, compound

HRID 1600189Notes

Reaction equation

HRID 1600189 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([CH2:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:27]([CH3:38])=[C:26]2[CH2:39][N:40]1[CH:44]=[CH:43][N:42]=[CH:41]1)(O)=O.C([N:47]([CH2:50]C)CC)C.[CH2:52]([OH:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>O1CCOCC1>[CH2:52]([O:59][C:50]([NH:47][CH2:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35])[C:27]([CH3:38])=[C:26]2[CH2:39][N:40]1[CH:44]=[CH:43][N:42]=[CH:41]1)=[O:8])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18926518HCID 18926518, compound

Product 1

HCID 18926524HCID 18926524, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Diphenylphosphoryl azide (0.744 g) was added to a mixture of methyl 5-(2-carboxyethyl)-3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indole-1-propanoate (1.0 g) and triethylamine (0.274 g) in dry dioxan (5 ml) at 50° C. The solution was then heated at 100° C. for 1 hour to give a clear solution. Benzyl alcohol (0.352 g) was added and the solution was heated at 1000° C. for a further 20 hours and then evaporated. The residue was partitioned between ethyl acetate and sodium bicarbonate solution. The organic layer was separated, washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel using dichloromethane/methanol (97:3) as eluent. The product fractions were combined and evaporated to give the title compound as a gum (0.41 g). Found: C,68.12; H,6.41; N,11.23. C27H30N4O4 requires: C,68.33; H,6.37; N,11.81%.

Workup

  1. customto give a clear solution
  2. temperaturethe solution was heated at 1000° C. for a further 20 hours
  3. customevaporated
  4. customThe residue was partitioned between ethyl acetate and sodium bicarbonate solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue was chromatographed on silica gel
  10. customevaporated

Sources & evidence

ORD record
ord-01e9389c18ea4cb69976242d7b72a793
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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