Trifluoroacetic acid → HCID 86290845, compound

HRID 525816Notes

Reaction equation

HRID 525816 reaction equation
[CH2:1]([NH:3][C:4](=[O:47])[C@@H:5]([NH:15][C:16]([C:18]1[S:26][C:25]2[C:20](=[N:21][CH:22]=[CH:23][C:24]=2[O:27][C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:37][C:38]3[CH:43]=[C:42]([CH3:44])[CH:41]=[CH:40][C:39]=3[F:45])=[O:36])=[C:30]([F:46])[CH:29]=2)[CH:19]=1)=[O:17])[CH2:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9])[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([NH:3][C:4](=[O:47])[C@@H:5]([NH:15][C:16]([C:18]1[S:26][C:25]2[C:20](=[N:21][CH:22]=[CH:23][C:24]=2[O:27][C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:37][C:38]3[CH:43]=[C:42]([CH3:44])[CH:41]=[CH:40][C:39]=3[F:45])=[O:36])=[C:30]([F:46])[CH:29]=2)[CH:19]=1)=[O:17])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86290884HCID 86290884, compound

Product 1

HCID 86290845HCID 86290845, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of tert-butyl (4S)-5-(ethylamino)-4-[({7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]-5-oxopentanoate (70 mg, 0.10 mmol) in 5 ml of methylene chloride was added 2 ml of trifluoroacetic acid. The mixture was stirred at room temperature for 2 hours and evaporated to dryness under reduced pressure. The residue was re-dissolved in MeOH (5 ml) and poured into 100 ml of water with vigorous stirring. The precipitates were filtered, washed with water and dried in vacuo to give (4S)-5-(ethylamino)-4-[({7-[3-fluoro-4-({[(2-fluoro-5-methylphenyl)amino]carbonyl}amino)phenoxy]thieno[3,2-b]pyridin-2-yl}carbonyl)amino]-5-oxopentanoic acid as light yellow solid. Yield: 53 mg, 83%.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue was re-dissolved in MeOH (5 ml)
  3. additionpoured into 100 ml of water with vigorous stirring
  4. filtrationThe precipitates were filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-b323ba0ac25e4ef29b01458a9cf48d78
Source dataset
uspto-grants-2016_05
Patent number
US09340555B2

Reaction notes

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