Potassium Acetate → HCID 67270043, compound

HRID 1695544Notes

Reaction equation

HRID 1695544 reaction equation
[OH:1][C@@H:2]1[C@H:15]2[C@@H:6]([CH2:7][CH2:8][C:9]3[C@:14]2([CH3:16])[CH2:13][CH:12]([CH:17]=O)[C:11](=O)[CH:10]=3)[C@@H:5]2[CH2:20][CH2:21][C@:22]3([C:26]4([CH2:30][O:29][CH2:28][O:27]4)[O:25][CH2:24][O:23]3)[C@@:4]2([CH3:31])[CH2:3]1.Cl.[F:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1[NH:41][NH2:42].C([O-])(=O)C.[K+]>C(O)C.O>[F:33][C:34]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:35]=1[N:41]1[C:11]2[CH:10]=[C:9]3[CH2:8][CH2:7][C@H:6]4[C@H:15]([C@:14]3([CH3:16])[CH2:13][C:12]=2[CH:17]=[N:42]1)[C@H:2]([OH:1])[CH2:3][C@@:4]1([CH3:31])[C@@:22]2([CH2:21][CH2:20][C@H:5]41)[C:26]1([CH2:30][O:29][CH2:28][O:27]1)[O:25][CH2:24][O:23]2

Participants

6

Reactant 3

HCID 517044Potassium AcetateHCID 27333012,4-Difluorophenylhydrazine hydrochlorideHCID 59810282HCID 59810282, compound

Product 1

HCID 67270043HCID 67270043, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

(8S,9S,10R,11S,13S,14S,17R)-11-hydroxy-10,13-dimethyl-3-oxo-1,2,3,6,7,8,9,10,11,12,13,14,15,16-tetradecahydrodispiro[cyclopenta[a]phenanthrene-17,4′-[1,3]dioxolane-5′,4″-[1,3]dioxolane]-2-carbaldehyde (Steroids 2003, (68), 177-191) (400 mg, 0.92 mmol) was dissolved in ethanol (10 ml) and water (1 ml). (2,4-difluorophenyl)hydrazine hydrochloride (167 mg, 0.92 mmol) and potassium acetate (160 mg, 1.63 mmol)) were added and the mixture was heated under microwave irradiation at 90° C. for 20 minutes. The mixture was partitioned between EtOAc (10 ml) and water (10 ml). The organic phase was washed with water (2 times 10 ml) and brine (5 ml) and was dried over Mg2SO4. Filtration followed by evaporation of the solvent gave 297 mg of the crude compound which was used as such without further purification. APCI-MS m/z: 541 [MH+].

Workup

  1. customThe mixture was partitioned between EtOAc (10 ml) and water (10 ml)
  2. washThe organic phase was washed with water (2 times 10 ml) and brine (5 ml)
  3. dry with materialwas dried over Mg2SO4
  4. filtrationFiltration
  5. customfollowed by evaporation of the solvent

Sources & evidence

ORD record
ord-8ae4b820b1984918af1cbdd14b8f880e
Source dataset
uspto-grants-2012_04
Patent number
US08163724B2

Reaction notes

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