HCID 68636737, compound → HCID 25125758, compound

HRID 1929789Notes

Reaction equation

HRID 1929789 reaction equation
[Si]([O:8][CH2:9][C:10](=[CH2:42])[C:11]([N:13]1[CH2:18][CH2:17][CH:16]([O:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][C:29]=2[O:30][CH3:31])[N:26]=[CH:25][N:24]=[C:23]3[NH:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[C:35]([Cl:40])[C:34]=2[F:41])[CH2:15][CH2:14]1)=[O:12])(C(C)(C)C)(C)C>O1CCCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:40][C:35]1[C:34]([F:41])=[C:33]([NH:32][C:23]2[C:22]3[C:27](=[CH:28][C:29]([O:30][CH3:31])=[C:20]([O:19][CH:16]4[CH2:17][CH2:18][N:13]([C:11](=[O:12])[C:10]([CH2:9][OH:8])=[CH2:42])[CH2:14][CH2:15]4)[CH:21]=3)[N:26]=[CH:25][N:24]=2)[CH:38]=[CH:37][C:36]=1[Cl:39]

Participants

4

Reactant 1

HCID 68636737HCID 68636737, compound

Product 1

HCID 25125758HCID 25125758, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

140 mg of the compound obtained in step 3) was diluted with 3 ml of tetrahydrofuran, and 1.1 ml of a 1.0M tetra-n-butyl ammonium fluoride-containing tetrahydrofuran solution was added thereto. The resulting mixture was incubated at room temperature for three hours. After the reaction terminated, a saturated sodium hydrogen carbonate was added, and the resulting solution was extracted twice with chloroform. The organic layer was dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate:methylene chloride:methanol=7:7:1) to obtain the title compound (58 mg, 51%).

Workup

  1. additionwas added
  2. customAfter the reaction terminated
  3. additiona saturated sodium hydrogen carbonate was added
  4. extractionthe resulting solution was extracted twice with chloroform
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationdistilled under a reduced pressure
  8. customThe resulting residue was purified by column chromatography (ethyl acetate:methylene chloride:methanol=7:7:1)

Sources & evidence

ORD record
ord-75473993af0e4eee876a2fb768ffb83e
Source dataset
uspto-grants-2012_05
Patent number
US08188102B2

Reaction notes

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