Water → HCID 58124888, compound

HRID 1971753Notes

Reaction equation

HRID 1971753 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH2:15][C:16]([N:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:19][CH2:20][C:21]([CH3:26])([CH3:25])[CH2:22][C:23]#[CH:24])=[O:17])[CH:9]2C(O)=O)=[CH:4][C:3]=1[O:31][CH3:32].O.[NH4+].[OH-]>C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+]>[C:27]([N:18]1[CH2:19][CH2:20][C:21]([CH3:25])([CH3:26])[CH2:22][C:23]2[CH:24]=[C:9]3[C:10]4[CH:11]=[C:2]([Br:1])[C:3]([O:31][CH3:32])=[CH:4][C:5]=4[CH2:6][CH2:7][N:8]3[C:15]=2[C:16]1=[O:17])([CH3:30])([CH3:29])[CH3:28]

Participants

6

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 58124938HCID 58124938, compound

Product 1

HCID 58124888HCID 58124888, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 517045Sodium AcetateSolvent

Procedure

A solution of 350 mg of 24g in 5 ml of acetic anhydride and 300 mg of sodium acetate, was heated at 90-100° C. for 3 h. The reaction was cooled to rt and 10 ml of water was added and stirring at ambient temperature was prolonged for 1 hr. The mixture was neutralized by addition of cold conc. NH4OH and the product was extracted with ethyl acetate. The organic extract was washed with water, dried and concentrated, and the remainders chromatographed over silicagel (using a gradient of heptane/ethyl acetate as eluent), to give 70 mg 24h (white crystalline material, triturated with heptane); Mp 175-177° C. Rf (heptane/ethyl acetate 1/1) 0.75.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe remainders chromatographed over silicagel (

Sources & evidence

ORD record
ord-457774a286dd4336babe42af7958b131
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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