4-Methylmorpholine → HCID 131725786, compound

HRID 1391408Notes

Reaction equation

HRID 1391408 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.N[CH2:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:35]>CN(C=O)C.CCOCC>[C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:35])[CH3:33].[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

7

Reactant 4

HCID 79724-MethylmorpholineHCID 11952PhenacylamineHCID 62365Isobutyl chloroformateHCID 171548Biotin

Product 1

HCID 131725786HCID 131725786, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 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 2-aminoacetophenone (824 mg, 6.10 mmol) is added. The solution is maintained stirred at room temperature for 3 h 30 min, 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 precipitate obtained is filtered and washed with water. Recrystallization is carried out by dissolving the product in MeOH in the hot state and reprecipitating by addition of water. The precipitate is filtered, washed with water, and then with ether to give 1.1 g (2.95 mmol, 72%) of crude product 1c.

Workup

  1. temperatureThe solution is maintained
  2. stirringstirred at room temperature for 3 h 30 min
  3. customevaporated to dryness
  4. customThe precipitate obtained
  5. filtrationis filtered
  6. washwashed with water
  7. customThe precipitate obtained
  8. filtrationis filtered
  9. washwashed with water
  10. customRecrystallization
  11. dissolutionby dissolving the product in MeOH in the hot state
  12. customreprecipitating by addition of water
  13. filtrationThe precipitate is filtered
  14. washwashed with water

Sources & evidence

ORD record
ord-3ba856c4ee3e4368a078338fa343b259
Source dataset
uspto-grants-2008_03
Patent number
US07338805B2

Reaction notes

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