Hydrochloric Acid → HCID 25056059, compound

HRID 908591Notes

Reaction equation

HRID 908591 reaction equation
[CH:1]([C:4]1[CH:37]=[CH:36][C:7]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][N:16]([C:18](=[O:20])[CH3:19])[CH2:15][CH2:14][N:13]2[S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[C:26](I)[CH:25]=2)(=[O:23])=[O:22])=[O:11])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[Br-].C([O:41][C:42](=[O:47])[CH2:43][CH2:44][CH2:45][Zn+])C.O1CCCC1.Cl>O1CCCC1.C1([C-]2C(C3C=CC=CC=3)=C(C3C=CC=CC=3)C(C3C=CC=CC=3)=C2C2C=CC=CC=2)C=CC=CC=1.C(P(C(C)(C)C)[C-]1C=CC=C1)(C)(C)C.[Fe+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[C:18]([N:16]1[CH2:15][CH2:14][N:13]([S:21]([C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:33])([F:32])[F:34])=[C:26]([CH2:45][CH2:44][CH2:43][C:42]([OH:47])=[O:41])[CH:25]=2)(=[O:22])=[O:23])[C@@H:12]([C:10](=[O:11])[NH:9][CH2:8][C:7]2[CH:36]=[CH:37][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)[CH2:17]1)(=[O:20])[CH3:19]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 25055803HCID 25055803, compoundHCID 178420673HCID 178420673, compound

Product 1

HCID 25056059HCID 25056059, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 129828017Ditert-butyl(cyclopenta-2,4-dien-1-yl)phosphane;iron(2+);(2,3,4,5-tetraphenylcyclopenta-1,4-dien-1-yl)benzeneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon stream, to a suspension of the compound (46 mg) obtained in Example 10, 1,2,3,4,5-pentaphenyl-1′-(di-tert-butylphosphino)ferrocene (5 mg) and bis(dibenzylideneacetone)palladium(0) (4 mg) in tetrahydrofuran was added, with stirring under ice-cooling, 0.5M 4-ethoxy-4-oxobutylzinc bromide/tetrahydrofuran solution (422 μl). After stirring at room temperature for 24 hr, 1N aqueous hydrochloric acid solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtrated and concentrated under reduced pressure. Methanol (0.5 ml) was added to the residue, and 4N aqueous sodium hydroxide solution (35 μl) was added with stirring under ice-cooling. After stirring at room temperature for 3 hr, 2N aqueous hydrochloric acid solution (70 μl) was added, and the mixture was concentrated under reduced pressure. The residue was purified by thin layer chromatography (chloroform:methanol:acetic acid=90:10:1) and recrystallized from water-containing methanol to give the title compound (2.4 mg).

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringAfter stirring at room temperature for 24 hr
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. additionMethanol (0.5 ml) was added to the residue, and 4N aqueous sodium hydroxide solution (35 μl)
  9. additionwas added
  10. stirringwith stirring under ice-
  11. temperaturecooling
  12. stirringAfter stirring at room temperature for 3 hr
  13. addition2N aqueous hydrochloric acid solution (70 μl) was added
  14. concentrationthe mixture was concentrated under reduced pressure
  15. customThe residue was purified by thin layer chromatography (chloroform:methanol:acetic acid=90:10:1)
  16. customrecrystallized from water-
  17. additioncontaining methanol

Sources & evidence

ORD record
ord-ea09209f8fda4a7787b0fd895f404079
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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