Ammonium Hydroxide → HCID 58124925, compound

HRID 1971728Notes

Reaction equation

HRID 1971728 reaction equation
[C:1]([N:5]([CH2:29][CH2:30][O:31][CH2:32][C:33]#C)[C:6](=[O:28])[C:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][C:13]([O:21][CH:22]([CH3:24])[CH3:23])=[C:14]([O:19][CH3:20])[CH:15]=2)[CH:10]1[C:25](O)=O)=O)([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+].[NH4+].[OH-]>C(OC(=O)C)(=O)C.O>[C:1]([N:5]1[C:6](=[O:28])[C:7]2[N:9]3[CH2:18][CH2:17][C:16]4[CH:15]=[C:14]([O:19][CH3:20])[C:13]([O:21][CH:22]([CH3:23])[CH3:24])=[CH:12][C:11]=4[C:10]3=[CH:25][C:33]=2[CH2:32][O:31][CH2:30][CH2:29]1)([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 517045Sodium AcetateHCID 58124953HCID 58124953, compound

Product 1

HCID 58124925HCID 58124925, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 264 mg of 18b and 500 mg of anhydrous sodium acetate in 7 ml of acetic anhydride was heated under N2 at 100° C. for 40 min. The mixture was cooled and diluted with 15 ml of water and stirred for 1 hr at ambient temperature. The mixture was then neutralized by dropwise addition of cold conc. aq. NH4OH and the product was extracted with ethyl acetate. The organic layer was washed with water, dried, concentrated and the residue was treated with diisopropyl ether to give 180 mg of 18c white crystalline material. Mp 125-127° C. MS-ESI: [M+1] 413.17.

Workup

  1. temperatureThe mixture was cooled
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. additionthe residue was treated with diisopropyl ether

Sources & evidence

ORD record
ord-546299a3bde2475f82b9c232d1445d7a
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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