Ammonia → HCID 58124845, compound

HRID 1971734Notes

Reaction equation

HRID 1971734 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([C:15](=O)[C:16](N(C(C)(C)C)CCCCC#C)=[O:17])[CH:9]2[C:12](O)=O)=[CH:4][C:3]=1[O:30][CH3:31].[C:32]([O-])(=O)C.[Na+].C(OC(=O)C)(=O)C.[NH3:44].CC[CH2:47][CH2:48][CH2:49][CH2:50][CH3:51].C(O[CH:56]([CH3:58])[CH3:57])(C)C>O>[C:56]([N:44]1[CH2:47][CH2:48][CH2:49][CH2:50][C:51]2[CH:12]=[C:9]3[C:10]4[CH:11]=[C:2]([Br:1])[C:3]([O:30][CH3:31])=[CH:4][C:5]=4[CH2:6][CH2:7][N:8]3[C:15]=2[C:16]1=[O:17])([CH3:58])([CH3:32])[CH3:57]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 7918Acetic Anhydride2×HCID 517045Sodium AcetateHCID 22997467HCID 22997467, compoundHCID 58124942HCID 58124942, compound

Product 1

HCID 58124845HCID 58124845, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 420 g of 19c and 500 mg of sodium acetate and 8 ml of acetic anhydride was heated at 105° C. for 3 h. The reaction mixture was cooled and diluted with 20 ml of water and stirred for 1 h to decompose the acetic anhydride. Then a solution of cold conc. ammonia was added to pH 8. The product was extracted with ethyl acetate. The organic layer was washed, dried, concentrated and the crude material was chromatographed over silica gel, using a gradient of heptane/ethyl acetate as eluent. The material thus isolated was treated with heptane/diisopropyl ether (1/1) to provide 95 mg of 19d as white crystalline material; Mp 127-129° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted with ethyl acetate
  3. washThe organic layer was washed
  4. customdried
  5. concentrationconcentrated
  6. customthe crude material was chromatographed over silica gel
  7. customThe material thus isolated

Sources & evidence

ORD record
ord-b7aff978435241788a244200db87c1ef
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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