Trifluoroacetic acid → HCID 18661316, compound

HRID 965277Notes

Reaction equation

HRID 965277 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:13][C:14](=O)[C:15]1[CH:20]=[CH:19][C:18]([C:21]([O:23]C(C)(C)C)=[O:22])=[CH:17][C:16]=1[NH2:28])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(O)=O.[Na+].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C>CN(C=O)C.C(Cl)Cl.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([OH:23])=[O:22])=[CH:17][C:16]=2[NH:28][C:10]1=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 90495Di-tert-butyl dicarbonateHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 18661315HCID 18661315, compound

Product 1

HCID 18661316HCID 18661316, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the above (11) (0.71 mMol) in dry DMF (20 mL) at 0° C. in a dewar flask was added triethylamine (200 mL, 1.42 mMol), NaHCO3 (300 mg, 3.57 mMol), and finally diphenylphosphorylazide (250 mL, 1.2 mMol). After stirring at 0° C. for 24 h the reaction was evaporated under reduced pressure, taken up in ethyl acetate (100 mL), washed with H2O, brine, dried (MgSO4), filtered and evaporated. The remaining residue was purified by silica gel chromatography eluted with ethyl acetate in hexane. The fully protected intermediate obtained was then treated with 50% trifluoroacetic acid in CH2Cl2 (15 mL) for 45 min. at room temperature, evaporated under reduced pressure, triturated with ether, filtered and dried under vacuum to give the fully deprotected intermediate. This was treated with di-t-butyldicarbonate and triethylamine overnight at room temperature in DMF, evaporated under reduced pressure, taken up into ethyl acetate and washed with 1N NaHSO4, water and brine, dried (MgSO4), filtered and evaporated. The residue was purified by silica gel chromatography eluted with ethyl acetate in hexane to give the title product (12).

Workup

  1. customwas evaporated under reduced pressure
  2. washwashed with H2O, brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe remaining residue was purified by silica gel chromatography
  7. washeluted with ethyl acetate in hexane
  8. customThe fully protected intermediate obtained
  9. customevaporated under reduced pressure
  10. customtriturated with ether
  11. filtrationfiltered
  12. customdried under vacuum
  13. customto give the fully deprotected intermediate
  14. customevaporated under reduced pressure
  15. washwashed with 1N NaHSO4, water and brine
  16. dry with materialdried (MgSO4)
  17. filtrationfiltered
  18. customevaporated
  19. customThe residue was purified by silica gel chromatography
  20. washeluted with ethyl acetate in hexane

Sources & evidence

ORD record
ord-3dd341362e6b429e93e4e6005ffff326
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

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