Water → HCID 11670326, compound

HRID 1713027Notes

Reaction equation

HRID 1713027 reaction equation
C[O:2][C:3](=[O:34])[CH2:4][N:5]([C:7](=[O:33])[CH2:8][C:9]([CH3:32])([CH3:31])[CH2:10][N:11]1[C:28](=[S:29])[N:14]2[C:15]3[CH:16]=[C:17]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)[O:18][C:19]=3[CH:20]=[C:13]2[C:12]1=[O:30])[CH3:6].O.C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+]>C(O)(C(F)(F)F)=O.CO>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:17]2[O:18][C:19]3[CH:20]=[C:13]4[C:12](=[O:30])[N:11]([CH2:10][C:9]([CH3:31])([CH3:32])[CH2:8][C:7]([N:5]([CH2:4][C:3]([OH:34])=[O:2])[CH3:6])=[O:33])[C:28](=[S:29])[N:14]4[C:15]=3[CH:16]=2)=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 11497027HCID 11497027, compound

Product 1

HCID 11670326HCID 11670326, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
40 °C

Procedure

Compound 20 was dissolved in TFA (1.5 ml) and water (0.75 ml) was added thereto. The resulting mixture was stirred at 40° C. for 16 hours. After cooling the mixture to room temperature, water and chloroform were added, followed by addition of 10% NaHCO3 (20 ml), while maintaining an acidic pH of the solution. The organic layer was separated, washed twice with water, dried over Na2SO4 and the solvent was evaporated under reduced pressure to give an orange solid. Chromatography purification was carried out using with a 8:2 ethyl acetate:methanol mixture as eluent to give Compound 21 (38.3 mg, 88% yield) as a yellow solid.

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. temperaturewhile maintaining an acidic pH of the solution
  3. customThe organic layer was separated
  4. washwashed twice with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure
  7. customto give an orange solid
  8. customChromatography purification

Sources & evidence

ORD record
ord-8eae679ba8e841b2903be103be0951a2
Source dataset
uspto-grants-2010_09
Patent number
US07795255B2

Reaction notes

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