Trifluoroacetic acid → HCID 86639753, compound

HRID 1811751Notes

Reaction equation

HRID 1811751 reaction equation
[C:1]([O:5][C:6](=[O:47])[C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([S:19][CH2:20][CH2:21][NH:22][C:23](=[O:43])[CH:24]([NH:35]C(OC(C)(C)C)=O)[CH2:25][CH2:26][NH:27]C(OC(C)(C)C)=O)[N:16]=[C:15]([NH2:44])[N:14]=2)[C:10]([CH3:45])=[CH:9][C:8]=1[CH3:46])([CH3:4])([CH3:3])[CH3:2].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51]>ClCCl>[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[F:48][C:49]([F:54])([F:53])[C:50]([OH:52])=[O:51].[C:1]([O:5][C:6](=[O:47])[C:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([S:19][CH2:20][CH2:21][NH:22][C:23](=[O:43])[CH:24]([NH2:35])[CH2:25][CH2:26][NH2:27])[N:16]=[C:15]([NH2:44])[N:14]=2)[C:10]([CH3:45])=[CH:9][C:8]=1[CH3:46])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59224655HCID 59224655, compound

Product 1

HCID 86639753HCID 86639753, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

5-{2-Amino-6-[2-(2,4-bis-tert-butoxycarbonylaminobutyrylamino)ethylsulfanyl]pyrimidin-4-yl}-2,4-dimethylbenzoic acid tert-butyl ester obtained in Step 2 above was dissolved in dichloromethane (37 ml). After the solution was cooled to 0° C., trifluoroacetic acid (13 ml) was added thereto. The reaction solution was gradually warmed to room temperature, and then stirred at room temperature for six hours. After the solvent was distilled off under reduced pressure, dichloromethane (10 ml) was added to the residue and again concentrated under reduced pressure. The resulting residue was suspended in ethyl acetate (60 ml). After the suspension was stirred at room temperature for two hours, the insoluble material was collected by filtration. The obtained solid was dried under reduced pressure to yield 5-{2-amino-6-[2-(2,4-diaminobutyrylamino)ethylsulfanyl]pyrimidin-4-yl}-2,4-dimethylbenzoic acid tert-butyl ester tri(trifluoroacetate) (3.6 g) as a white solid material.

Workup

  1. temperatureThe reaction solution was gradually warmed to room temperature
  2. distillationAfter the solvent was distilled off under reduced pressure, dichloromethane (10 ml)
  3. additionwas added to the residue
  4. concentrationagain concentrated under reduced pressure
  5. stirringAfter the suspension was stirred at room temperature for two hours
  6. filtrationthe insoluble material was collected by filtration
  7. customThe obtained solid was dried under reduced pressure

Sources & evidence

ORD record
ord-d92bbb40bbdd420b91ee718935d07930
Source dataset
uspto-grants-2013_01
Patent number
US08362236B2

Reaction notes

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