HCID 66615069, compound → HCID 46199361, compound

HRID 717621Notes

Reaction equation

HRID 717621 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]>C(O)(C(F)(F)F)=O.C(Cl)Cl.CCO>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]([OH:24])=[O:23])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 1

HCID 66615069HCID 66615069, compound

Product 1

HCID 46199361HCID 46199361, compoundYield 47%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product of Step E (0.05 g; 0.129 mmol) in 60% TFA in CH2Cl2 (5 ml) was refluxed for 2 h, cooled to room temperature then diluted to 7 ml with EtOH. The resulting mixture was evaporated to dryness under reduced pressure kept in vacuo for 1 h. The residue was treated dissolved in EtOH (2 ml) and 3 drops of concentrated NH4OH was added. The resulting mixture was partially concentrated under reduced pressure and the precipitate, formed was filtered off, washed with Et2O and dried to give the titled compound (0.02 g; 47%) as colourless solid. 1H-NMR (CD3OD+CDCl3) 7.07 (d, 2H, J=8.6 Hz); 6.86 (d, 2H, J=8.6 Hz); 4.63 (s, CD3OH); 3.58 (s, 2H); 3.38 (m, 8H); 2.49 (t, 2H, J=7.8 Hz); 1.53 (m, 2H); 1.24 (m, 10H); 0.83 (m, 3H).

Workup

  1. customThe resulting mixture was evaporated to dryness under reduced pressure
  2. additionThe residue was treated
  3. dissolutiondissolved in EtOH (2 ml)
  4. addition3 drops of concentrated NH4OH was added
  5. concentrationThe resulting mixture was partially concentrated under reduced pressure
  6. customthe precipitate, formed
  7. filtrationwas filtered off
  8. washwashed with Et2O
  9. customdried

Sources & evidence

ORD record
ord-6f0083567d0943eda3e8c3f084f1bbc3
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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