Water → HCID 54437838, compound

HRID 1780507Notes

Reaction equation

HRID 1780507 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:28])([C:7]3[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:27])[C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N+:24]([O-])=O)[CH:19]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:29].O>C(OCC)(=O)C.CO.[Cl-].[Cl-].[Cl-].[Ti+3]>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:28])([C:7]3[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:27])[C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([NH2:24])[CH:19]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:29]

Participants

6

Reactant 2

HCID 962WaterHCID 54295182HCID 54295182, compound

Product 1

HCID 54437838HCID 54437838, compound

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 200 mg portion of the product of Example 268 was dissolved in ethyl acetate and methanol. Twenty ml of 20% aqueous titanium trichloride was added, the flask was evacuated and the mixture was stirred at ambient temperature for 16 h. The mixture was then made basic with ammonium hydroxide, resulting in an exotherm and the formation of a dark solid. Water was added to break up the solid, and the mixture was extracted with dichloromethane. The remaining reaction mixture was filtered, and the solid filter cake was washed with dichloromethane. The organic layers were collected, dried and concentrated under vacuum. The residue was recrystallized from dichloromethane/hexane to obtain 190 mg of the desired product. It was purified by chromatography over silica gel, eluting with ethyl acetate going to 10% methanol/ethyl acetate, and recrystallized again from dichloromethane/hexane to obtain 80.5 mg of purified product, m.p. 154°-156°. FDMS: m/e=363.

Workup

  1. customthe flask was evacuated
  2. customresulting in an exotherm
  3. extractionthe mixture was extracted with dichloromethane
  4. customThe remaining reaction mixture
  5. filtrationwas filtered
  6. filtrationthe solid filter cake
  7. washwas washed with dichloromethane
  8. customThe organic layers were collected
  9. customdried
  10. concentrationconcentrated under vacuum
  11. customThe residue was recrystallized from dichloromethane/hexane

Sources & evidence

ORD record
ord-57d4862854114ce7b5bd585f3689d772
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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