Ammonium Acetate → HCID 44535824, compound

HRID 268617Notes

Reaction equation

HRID 268617 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=2)=O)=[CH:4][C:3]=1[O:32][CH3:33].C([O-])(=O)C.[NH4+:38]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:38][C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])=[CH:15][CH:14]=3)=[CH:10][C:9]=2[C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)=[CH:4][C:3]=1[O:32][CH3:33]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 69313935HCID 69313935, compound

Product 1

HCID 44535824HCID 44535824, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the product of Example 1 Step 2 (420 mg, 0.9 mmol) and ammonium acetate (750 mg, 9.7 mmol) in glacial acetic acid (15 ml) was heated under reflux for 16 hours. After cooling to room temperature, the reaction mixture was concentrated and aqueous sodium hydrogen carbonate solution was added. The mixture was extracted with chloroform and the organic phase washed with water and brine, dried and concentrated in vacuo to give the title compound; MS(ES+) m/e 448,450 [+H]+.

Workup

  1. temperatureunder reflux for 16 hours
  2. concentrationthe reaction mixture was concentrated
  3. additionaqueous sodium hydrogen carbonate solution was added
  4. extractionThe mixture was extracted with chloroform
  5. washthe organic phase washed with water and brine
  6. customdried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e4dbf64de174f25b1140d10ef15f3b6
Source dataset
uspto-grants-2008_11
Patent number
US07446106B2

Reaction notes

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