Ammonia → HCID 86628207, compound

HRID 1821364Notes

Reaction equation

HRID 1821364 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:18][C:19]([NH2:21])=[S:20])=[N:2]1.C(O)C.Br[CH2:26][C:27](=O)[C:28]([O:30][CH2:31][CH3:32])=[O:29].N>>[CH2:31]([O:30][C:28]([C:27]1[N:21]=[C:19]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2/[CH:11]=[CH:10]/[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][N:2]=2)[S:20][CH:26]=1)=[O:29])[CH3:32]

Participants

5

Reactant 4

HCID 222AmmoniaHCID 702EthanolHCID 66144Ethyl bromopyruvateHCID 86628203HCID 86628203, compound

Product 1

HCID 86628207HCID 86628207, compoundYield 17%

Procedure

Compound 161 (0.40 g, 1.4 mmol) was added with ethanol (3.0 mL, 1.5 mmol) and ethyl bromopyruvate (0.10 mL, 0.8 mmol) and after heating under reflux for 18 hours, aqueous ammonia was added to stop the reaction. The precipitated crude product was collected by filtration and purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/2). Then, the product was triturated in ethyl acetate to obtain Compound 169 (41 mg, 17%).

Workup

  1. temperatureafter heating
  2. temperatureunder reflux for 18 hours
  3. customthe reaction
  4. customThe precipitated crude product
  5. filtrationwas collected by filtration
  6. custompurified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/2)
  7. customThen, the product was triturated in ethyl acetate

Sources & evidence

ORD record
ord-716af4a3f075471ab6d445d6c08e5ba1
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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