Trifluoroacetic acid → HCID 18536046, compound

HRID 412141Notes

Reaction equation

HRID 412141 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[N:30]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34]([F:40])[CH:33]=4)[CH:29]=[N:28][CH:27]=3)[CH2:21][C:20]2=[O:41])=[CH:11][CH:10]=1)C1C=CC=CC=1.[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[H][H]>CO.CCOC(C)=O.[Pd]>[F:42][C:43]([F:48])([F:47])[C:44]([OH:46])=[O:45].[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][CH:15]=[C:16]2[N:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[N:30]([CH2:31][C:32]4[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[C:34]([F:40])[CH:33]=4)[CH:29]=[N:28][CH:27]=3)[CH2:21][C:20]2=[O:41])=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18536104HCID 18536104, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18536046HCID 18536046, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of the benzyl ether from Step F (1.563 g, 2.85 mmol) in 25 mL of 1:1 MeOH/EtOAc was added trifluoroacetic acid (1.0 mL) and 10% palladium on carbon (900 mg). The solution was stirred under a balloon atmosphere of hydrogen at room temperature. After 8 hours, the solution was filtered through celite, and the filter pad was rinsed with 1:1 MeOH/THF. Concentration in vacuo provided the titled product as a white foam which was used in the next reaction without further purification.

Workup

  1. filtrationthe solution was filtered through celite
  2. washthe filter pad was rinsed with 1:1 MeOH/THF
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-0b5bd304f75a407b8651c9ec7288a950
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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