Acetic Acid → HCID 58124871, compound

HRID 1971658Notes

Reaction equation

HRID 1971658 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:18]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]#[C:25][C:26]3[S:27][CH:28]=[CH:29][CH:30]=3)=[O:17])[CH:9]2C(O)=O)=[CH:4][C:3]=1[O:36][CH3:37].C(O)(=O)C.N>C(OC(=O)C)(=O)C.C([O-])(=O)C.[Na+].O>[Br:1][C:2]1[C:3]([O:36][CH3:37])=[CH:4][C:5]2[CH2:6][CH2:7][N:8]3[C:15]4[C:16](=[O:17])[N:18]([C:31]([CH3:33])([CH3:34])[CH3:32])[CH2:19][CH2:20][CH2:21][O:22][CH2:23][C:24]=4[C:25]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)=[C:9]3[C:10]=2[CH:11]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 222AmmoniaHCID 58124883HCID 58124883, compound

Product 1

HCID 58124871HCID 58124871, compoundYield 52.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 7918Acetic AnhydrideSolventHCID 517045Sodium AcetateSolvent

Conditions

Temperature
105 °C

Procedure

A solution of 257 mg of 7j in a mixture of 5 ml of acetic anhydride and 100 mg of sodium acetate was heated at 105° C. for 30 min. The reaction mixture was cooled, diluted with 20 ml of water and stirred for 1 hr at RT. Then, acetic acid was neuralized by addition of cold conc. ammonia. The product was extracted with ethyl acetate and the organic layer was washed twice with water, dried, concentrated and the crude material was purified by chromatography over silica gel, using a gradient of heptane/ethyl acetate. The material isolated was triturated with diethyl ether, to give 120 mg of 7k;

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe product was extracted with ethyl acetate
  3. washthe organic layer was washed twice with water
  4. customdried
  5. concentrationconcentrated
  6. customthe crude material was purified by chromatography over silica gel
  7. customThe material isolated
  8. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-4e957c0ad6564213ac9a48843a130a93
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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