HCID 58671549, compound → HCID 58671541, compound

HRID 2221097Notes

Reaction equation

HRID 2221097 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:17][C:18]1[C:23]([NH:24][C:25]([O:27]C(C)(C)C)=O)=[CH:22][N:21]=[C:20]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:19]=1)C(OC)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[O:27]=[C:25]1[CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:17][C:18]2[C:23](=[CH:22][N:21]=[C:20]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:19]=2)[NH:24]1

Participants

4

Reactant 1

HCID 58671549HCID 58671549, compound

Product 1

HCID 58671541HCID 58671541, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3E (980 mg, 1.94 mmol) in TFA (2 mL) and CH2Cl2 (2 mL) was stirred at RT for 2 h. After this time, no starting material was detected by LC-MS. The reaction was concentrated under reduced pressure. The resulting residue was diluted with EtOAc (30 mL) and washed with saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc (30 mL×3). The combined organic layers were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The resulting residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (30-100%) in hexane to give the title compound as a white solid (470 mg, 65%). LC/MS (method A): retention time=2.72 min, (M+H)+=374.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with EtOAc (30 mL)
  3. washwashed with saturated aqueous NaHCO3
  4. extractionThe aqueous layer was extracted with EtOAc (30 mL×3)
  5. washThe combined organic layers were washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by silica gel (40 g) column chromatography
  10. washeluting with a gradient of EtOAc (30-100%) in hexane

Sources & evidence

ORD record
ord-b4b12e5b592d442580462332fb7a11f2
Source dataset
uspto-grants-2008_05
Patent number
US07368458B2

Reaction notes

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