Trifluoroacetic acid → 5-(ethylamino)-4-({[5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol-3-yl]carbonyl}amino)-5-oxopentanoic acid

HRID 1402602Notes

Reaction equation

HRID 1402602 reaction equation
[CH2:1]([NH:3][C:4](=[O:45])[CH:5]([NH:15][C:16]([C:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([NH:36][C:37]([C:39]4[O:40][CH:41]=[CH:42][C:43]=4[CH3:44])=[O:38])[CH:31]=3)[CH:26]=[CH:25][N:24]=2)[NH:20][CH:19]=1)=[O:17])[CH2:6][CH2:7][C:8]([O:10]C(C)(C)C)=[O:9])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([NH:3][C:4](=[O:45])[CH:5]([NH:15][C:16]([C:18]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([NH:36][C:37]([C:39]4[O:40][CH:41]=[CH:42][C:43]=4[CH3:44])=[O:38])[CH:31]=3)[CH:26]=[CH:25][N:24]=2)[NH:20][CH:19]=1)=[O:17])[CH2:6][CH2:7][C:8]([OH:10])=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71293517tert-butyl 5-(ethylamino)-4-({[5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol-3-yl]carbonyl}amino)-5-oxopentanoate

Product 1

HCID 712936915-(ethylamino)-4-({[5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol-3-yl]carbonyl}amino)-5-oxopentanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 5-(ethylamino)-4-({[5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol-3-yl]carbonyl}amino)-5-oxopentanoate (34 mg, 0.055 mmol) in 5 ml of methylene chloride was added 2 ml of TFA. The mixture was stirred at room temperature for 1 hour, and evaporated to dryness under reduced pressure. The residue was re-dissolved in 5 ml of methanol and poured into 100 ml of water with vigorous stirring. The precipitates were filtered, washed with water and dried in vacuo to give 5-(ethylamino)-4-({[5-(4-{3-[(3-methyl-2-furoyl)amino]phenoxy}pyridin-2-yl)-1H-pyrrol-3-yl]carbonyl}amino)-5-oxopentanoic acid as white solid. Yield: 26 mg, 84%.

Workup

  1. customevaporated to dryness under reduced pressure
  2. dissolutionThe residue was re-dissolved in 5 ml of methanol
  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-d14beb2e8a1946698d2c717cfa705c4f
Source dataset
uspto-grants-2014_12
Patent number
US08906944B2

Reaction notes

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