Hydrochloric Acid → 5-(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)pentanoic acid

HRID 1778138Notes

Reaction equation

HRID 1778138 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C)=[O:19])([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([C:33]2[O:34][CH:35]=[CH:36][C:37]=2[CH3:38])=[O:32])[CH:25]=1.[OH-].[K+].Cl>C1COCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]=[S:11]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])([CH3:13])=[O:12])=[O:9])=[CH:4][C:3]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([C:33]2[O:34][CH:35]=[CH:36][C:37]=2[CH3:38])=[O:32])[CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 118130044Methyl 5-(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)pentanoate

Product 1

HCID 1181300375-(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)pentanoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of methyl 5-(N-{[6-amino-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-methylsulfonimidoyl)pentanoate (367 mg, 0.68 mmol) in THF (13 mL) at 0° C. was added dropwise 1N aq KOH (3.42 mL, 5 eq). The reaction was stirred at 0° C. for 20 minutes and then at RT for 4 hours. It was then cooled back to 0° C. and 2N aq HCl was dropwise added to adjust the pH to about 5-6. The mixture was then evaporated at RT to remove the most of the THF. The oily residue was then partitioned between aq NH4Cl and CHCl3. The chloroform layer was isolated, followed by a wash with brine (1×) and then dried with anhydrous Na2SO4 overnight. The upper clear solution was decanted, concentrated, and subject to a gradient column chromatography (MeOH-DCM 1:500 to 1:9). The corresponding product fractions were collected, concentrated, and treated with EtOAc with stirring. The title compound was obtained upon filtration as white solid (238 mg, 67%).

Workup

  1. waitat RT for 4 hours
  2. temperatureIt was then cooled back to 0° C.
  3. customThe mixture was then evaporated at RT
  4. customto remove the most of the THF
  5. customThe oily residue was then partitioned between aq NH4Cl and CHCl3
  6. customThe chloroform layer was isolated
  7. washa wash with brine (1×)
  8. dry with materialdried with anhydrous Na2SO4 overnight
  9. customThe upper clear solution was decanted
  10. concentrationconcentrated
  11. customThe corresponding product fractions were collected
  12. concentrationconcentrated
  13. additiontreated with EtOAc
  14. stirringwith stirring

Sources & evidence

ORD record
ord-7b8ea5db825b4a8aa395d241906cf546
Source dataset
uspto-grants-2016_02
Patent number
US09266869B2

Reaction notes

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