Water → 3-Deoxyviridicatin

HRID 2351323Notes

Reaction equation

HRID 2351323 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:16](OC(=O)C)(=[O:18])[CH3:17].[H-].[Na+].O>O1CCCC1.CN(C)C=O>[O:18]=[C:16]1[CH:17]=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]2[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=2)[NH:1]1

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 760802-Aminobenzophenone

Product 1

HCID 3759123-Deoxyviridicatin

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of o-amino benzophenone (10 g) and acetic acid anhydride (10 ml) in tetrahydrofuran (150 ml) was refluxed for 8 hours. The mixture was thereafter evaporated and the residue was partitioned between sat NaHC03, (20ml) and diethylether (l5Oml). The organic phase was dried and evaporated to give an yellow oil which was redissolved in dimethyl formamide (150ml). To this solution was added NaH (5g) and the mixture was stirred at ll0° C. for 11/2 hour, whereafter it was cooled to room temperature, and poured into water (300ml). This treatment afforded a precipitate of the title compound as pale crystals, which were collected by filtration. The crystals were washed with water and dried. M.p.244°-247° C..

Workup

  1. temperaturewas refluxed for 8 hours
  2. customThe mixture was thereafter evaporated
  3. customthe residue was partitioned
  4. customThe organic phase was dried
  5. customevaporated
  6. customto give an yellow oil which

Sources & evidence

ORD record
ord-d4731c76856d4ce78300e17c487e89ea
Source dataset
uspto-grants-1989_10
Patent number
US04873244

Reaction notes

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