HCID 136388729, compound → HCID 136388728, compound

HRID 1929790Notes

Reaction equation

HRID 1929790 reaction equation
[Cl:1][C:2]1[C:3]([F:33])=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([OH:32])=[C:17]([O:20][CH:21]4[CH2:24][N:23](C(OCCCC)=O)[CH2:22]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]>C(Cl)Cl.FC(F)(F)C(O)=O>[NH:23]1[CH2:24][CH:21]([O:20][C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][C:16]=2[OH:32])[N:13]=[CH:12][N:11]=[C:10]3[NH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[C:3]=2[F:33])[CH2:22]1

Participants

4

Reactant 1

HCID 136388729HCID 136388729, compound

Product 1

HCID 136388728HCID 136388728, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

100 mg of the compound obtained in step 1) was diluted with 2 ml of methylene chloride, and 0.2 ml of trifluoroacetic acid was added thereto. The resulting mixture was stirred at room temperature for one hour. After the reaction terminated, the resulting solution was distilled under a reduced pressure to remove a solvent. The resulting residue was alkalinized with a saturated sodium bicarbonate and extracted with a mixed solvent of chloroform and 2-propanol (3:1). The organic layer was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The resulting residue was purified by column chromatography (methylene chloride:methanol=10:1) to obtain the title compound (69 mg, 87%).

Workup

  1. additionwas added
  2. customAfter the reaction terminated
  3. distillationthe resulting solution was distilled under a reduced pressure
  4. customto remove a solvent
  5. extractionextracted with a mixed solvent of chloroform and 2-propanol (3:1)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationdistilled under a reduced pressure
  9. customThe resulting residue was purified by column chromatography (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-3c99663a18cf4d5a87a2e7e924ba2cf3
Source dataset
uspto-grants-2012_05
Patent number
US08188102B2

Reaction notes

Loading…