Trifluoroacetic acid → HCID 68322502, compound

HRID 1023571Notes

Reaction equation

HRID 1023571 reaction equation
CC([N:5]([C@@H:9]([C:14]([NH:16][C:17]1[CH:18]=[N:19][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([O:31][CH3:32])[CH:25]=2)=[CH:21][CH:22]=1)=[O:15])[C:10]([CH3:13])([CH3:12])[CH3:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O>ClCCl>[CH3:11][C:10]([CH3:13])([CH3:12])[C@H:9]([C:14]([NH:16][C:17]1[CH:18]=[N:19][C:20]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([O:31][CH3:32])[CH:25]=2)=[CH:21][CH:22]=1)=[O:15])[NH2:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86673599HCID 86673599, compound2×

Product 1

HCID 68322502HCID 68322502, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl((1R)-2,2-dimethyl-1-{[(6-{[4-methyl-3-(methyloxy)phenyl]oxy}-3-pyridinyl)amino]carbonyl}propyl)carbamate (Intermediate 96, 8.2 mg) in dry dichloromethane (0.5 mL) cooled to 0° C., TFA (57 μl, 0.740 mmol) was added dropwise and the solution was stirred for 3 hours at that temperature. The volatiles were evaporated. The residue was dissolved with dichloromethane (2 mL) and an aqueous saturated solution of NaHCO3 was added (4 mL). The layers were separated and the aqueous layer was extracted twice with dichloromethane. The gathered organic layers were dried over sodium sulphate and evaporated to afford the title compound (6.2 mg).

Workup

  1. customThe volatiles were evaporated
  2. dissolutionThe residue was dissolved with dichloromethane (2 mL)
  3. additionan aqueous saturated solution of NaHCO3 was added (4 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted twice with dichloromethane
  6. dry with materialThe gathered organic layers were dried over sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-5153e6ca61374b2bb9bee42825a486df
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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