HCID 67126415, compound → HCID 67126454, compound

HRID 573162Notes

Reaction equation

HRID 573162 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[CH:7]=[CH:6][C:5]=1[NH:14][CH2:15][CH:16]1[O:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17]1)([O-:3])=[O:2]>C(Cl)Cl.FC(F)(F)C(O)=O>[NH:18]1[CH2:19][CH2:20][O:21][CH:16]([CH2:15][NH:14][C:5]2[CH:6]=[CH:7][C:8]([S:10]([NH2:11])(=[O:12])=[O:13])=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:17]1

Participants

4

Reactant 1

HCID 67126415HCID 67126415, compound

Product 1

HCID 67126454HCID 67126454, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 369A (0.8 g) in methylene chloride (10 mL) and trifluoroacetic acid (10 mL) was stirred at room temperature for 2 hours. The solvents were evaporated and the residue was triturated with diethyl ether. The resulting solid was dissolved in 5% aqueous sodium carbonate solution (20 mL). The mixture was concentrated to dryness and the resulting solid was triturated with a solution of 10% methanol in methylene chloride several times. Evaporation of the organic solvent provided the title compound.

Workup

  1. customThe solvents were evaporated
  2. customthe residue was triturated with diethyl ether
  3. dissolutionThe resulting solid was dissolved in 5% aqueous sodium carbonate solution (20 mL)
  4. concentrationThe mixture was concentrated to dryness
  5. customthe resulting solid was triturated with a solution of 10% methanol in methylene chloride several times
  6. customEvaporation of the organic solvent

Sources & evidence

ORD record
ord-7434ee9a19e549b782e8f55c6bd73495
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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