Triethylamine → HCID 131729739, compound

HRID 1929533Notes

Reaction equation

HRID 1929533 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][C:5]([CH2:6][C:7]2[C:8]([CH3:15])=[C:9]([CH3:14])[C:10](=[O:13])[NH:11][N:12]=2)=[CH:4][C:3]=1C(N1CCN2C(C(F)(F)F)=NN=C2C1)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:40])C=CC=CC=1.CC[N:52]([CH2:55]C)CC.[C:57]([OH:61])([CH3:60])([CH3:59])[CH3:58].C1(C)C=CC=CC=1>>[C:57]([O:61][C:55](=[O:40])[NH:52][C:3]1[CH:4]=[C:5]([CH2:6][C:7]2[C:8]([CH3:15])=[C:9]([CH3:14])[C:10](=[O:13])[NH:11][N:12]=2)[CH:16]=[CH:17][C:2]=1[F:1])([CH3:60])([CH3:59])[CH3:58]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22595558Toluene tert-butyl alcoholHCID 68975739HCID 68975739, compound

Product 1

HCID 131729739HCID 131729739, compound

Procedure

To a mixture of Example 14, N4 in tert-BuOH:toluene (1:1, 0.171 M) was added diphenyl phosphoryl azide (2.2 eq) and Et3N (2.2 eq). The reaction was heated at reflux until consumption of the starting material and then volatiles were removed under reduced pressure. The resulting residue was partitioned between DCM and sat. aq. NaHCO3; the organic phase was separated, dried (Na2SO4) and filtered. Evaporation of the solvent provided yellow oil (O1) which was used as such in the next step without purification. MS (ES) C18H22FN3O3 required: 347. found: 348 (M+H)+.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux until consumption of the starting material
  3. customvolatiles were removed under reduced pressure
  4. customThe resulting residue was partitioned between DCM and sat. aq. NaHCO3
  5. customthe organic phase was separated
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customEvaporation of the solvent
  9. customprovided yellow oil (O1) which
  10. customwithout purification

Sources & evidence

ORD record
ord-47ed9e902409445db5e27b7552b6ae10
Source dataset
uspto-grants-2012_05
Patent number
US08188084B2

Reaction notes

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