Benzyl Alcohol → HCID 178453647, compound

HRID 1600676Notes

Reaction equation

HRID 1600676 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:15][CH2:14][C@H:13](C(O)=O)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([NH:21][C:24]([O:50][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[O:33])[CH2:14][CH2:15]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 178453624HCID 178453624, compound

Product 1

HCID 178453647HCID 178453647, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

5.5 g of trans-4-tert-butyloxycarbonylaminomethylcyclohexanecarboxylic acid are dissolved in 250 ml of dioxane and, after addition of 6.5 ml of triethylamine and 5.6 ml of diphenylphosphoryl azide, heated at 130° C. for 1.5 hours. Then 8.7 ml of benzyl alcohol are added and the mixture is heated to boiling for a further 48 hours. After cooling, the dioxane is distilled off in a rotary evaporator, the residue is taken up in ethyl acetate and, after washing with saturated sodium chloride solution and drying over magnesium sulphate, the solvent is distilled off in a rotary evaporator. The residue is triturated with petroleum ether/ether (5:1), filtered off with suction and dried.

Workup

  1. temperaturethe mixture is heated
  2. temperatureAfter cooling
  3. distillationthe dioxane is distilled off in a rotary evaporator
  4. washafter washing with saturated sodium chloride solution
  5. dry with materialdrying over magnesium sulphate
  6. distillationthe solvent is distilled off in a rotary evaporator
  7. customThe residue is triturated with petroleum ether/ether (5:1)
  8. filtrationfiltered off with suction
  9. customdried

Sources & evidence

ORD record
ord-722dc45023384159864d08758cc3b7e2
Source dataset
uspto-grants-1999_11
Patent number
US05977102

Reaction notes

Loading…