HCID 67126415, compound → HCID 67126454, compound

HRID 1518871Notes

Reaction equation

HRID 1518871 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 415A (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 solution was evaporated to dryness and the resulting solid was triturated with a solution of 10% methanol in dichloromethane several times. Evaporation of the organic solution gave 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. customThe solution was evaporated to dryness
  5. customthe resulting solid was triturated with a solution of 10% methanol in dichloromethane several times
  6. customEvaporation of the organic solution

Sources & evidence

ORD record
ord-f9767e7300304612ac1aaf08b294962a
Source dataset
uspto-grants-2015_07
Patent number
US09072748B2

Reaction notes

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