p-Aminoacetophenone → HCID 131725786, compound

HRID 1391407Notes

Reaction equation

HRID 1391407 reaction equation
[OH:1][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:3].CN1CCOCC1.ClC(OCC(C)C)=O.[CH3:32][C:33]([C:35]1[CH:40]=[CH:39][C:38](N)=[CH:37][CH:36]=1)=[O:34]>CN(C=O)C>[C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[O:34])[CH3:32].[OH:3][C:2]([CH2:4][CH2:5][CH2:6][CH2:7][C@H:8]1[C@@H:16]2[C@@H:11]([NH:12][C:13]([NH:15]2)=[O:14])[CH2:10][S:9]1)=[O:1]

Participants

6

Reactant 4

HCID 7468p-AminoacetophenoneHCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 171548Biotin

Product 1

HCID 131725786HCID 131725786, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The D-biotin (1 g, 4.1 mmol) is solubilized in 45 ml of anhydrous DMF in the hot state. The mixture is cooled to 0° C. under argon, and then N-methylmorpholine (590 μl, 5.33 mmol) and isobutyl chloroformate (840 μl, 6.60 mmol) are successively added. The mixture is kept stirred for 30 min, and then 4-aminoacetophenone (824 mg, 6.10 mmol) is added. The solution is maintained stirred at 0° C. for 2 h, and then evaporated to dryness. The residue is taken up in 50 ml of water. The precipitate obtained is filtered, washed with water and then with 50 ml of MeOH in the hot state. The white precipitate is dissolved in DMF while heating and then the solution obtained is filtered and washed with MeOH. The filtrate is recovered and evaporated to dryness to give 888 mg of 1b (2.46 mmol, 60%).

Workup

  1. temperatureThe solution is maintained
  2. stirringstirred at 0° C. for 2 h
  3. customevaporated to dryness
  4. customThe precipitate obtained
  5. filtrationis filtered
  6. washwashed with water
  7. dissolutionThe white precipitate is dissolved in DMF
  8. temperaturewhile heating
  9. customthe solution obtained
  10. filtrationis filtered
  11. washwashed with MeOH
  12. customThe filtrate is recovered
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-00c094cc66b046f495b3cc6eb980ef61
Source dataset
uspto-grants-2008_03
Patent number
US07338805B2

Reaction notes

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