HCID 58670138, compound → HCID 58670125, compound

HRID 2249504Notes

Reaction equation

HRID 2249504 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:18][C:19]1[C:24]([NH:25][C:26](OC(C)(C)C)=[O:27])=[CH:23][CH:22]=[C:21]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:20]=1)C(OCC)=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:26]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)[CH2:18][C:19]2[C:24](=[CH:23][CH:22]=[C:21]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[N:20]=2)[NH:25]1

Participants

4

Reactant 1

HCID 58670138HCID 58670138, compound

Product 1

HCID 58670125HCID 58670125, compoundYield 102.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1L (145 mg, 0.287 mmol) in TFA (1 mL) and CH2Cl2 (1 mL) was stirred at RT for 1 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 (40 mL) and washed with saturated aqueous NaHCO3 (20 mL). The aqueous layer was extracted with EtOAc (20 mL×2). The combined organic layers were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated to give the title compound as a white solid (110 mg, 100%). LC/MS (method A): retention time=3.09 min, (M+H)+=374.

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionThe resulting residue was diluted with EtOAc (40 mL)
  3. washwashed with saturated aqueous NaHCO3 (20 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (20 mL×2)
  5. washThe combined organic layers were washed with saturated NaCl
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2acc715a7e144326abc0c2898db672a7
Source dataset
uspto-grants-2008_01
Patent number
US07314882B2

Reaction notes

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