4-Methylmorpholine → Benzophenone

HRID 1828667Notes

Reaction equation

HRID 1828667 reaction equation
OC(CCCC[C@H]1[C@@H]2[C@@H](NC(N2)=O)CS1)=O.CN1CCOCC1.ClC(OCC(C)C)=O.N[C:33]1[CH:34]=[C:35]([CH:44]=[CH:45][CH:46]=1)[C:36]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)=[O:37]>CN(C=O)C>[C:36]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)(=[O:37])[C:35]1[CH:44]=[CH:45][CH:46]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 17817Methanone, (3-aminophenyl)phenyl-HCID 62365Isobutyl chloroformateHCID 171548Biotin

Product 1

HCID 3102BenzophenoneYield 112.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

The D-biotin (50 mg, 2.05 mmol) is solubilized in 23 ml of anhydrous DMF in the hot state. The mixture is cooled to 0° C. under argon, and then N-methylmorpholine (295 μl, 2.67 mmol) and isobutyl chloroformate (420 μl, 3.28 mmol) are successively added. The mixture is kept stirred for 30 min, and then 3-aminobenzophenone (605 mg, 3.07 mmol) and N-methylmorpholine (240 μl, 2.17 mmol) in 7 ml of DMF are added. The solution is maintained stirred at 0° C. for 2 h, and then evaporated to dryness. The residue is taken up in 1 ml of MeOH, and then 25 ml of water are added. The precipitate obtained is filtered, washed with water and then with ether to give 810 mg (93%) of crude product 1d. Recrystallization from the MeOH—H2O pair gives 1d (630 mg, 72%) in the form of a white powder.

Workup

  1. temperatureThe solution is maintained
  2. stirringstirred at 0° C. for 2 h
  3. customevaporated to dryness
  4. addition25 ml of water are added
  5. customThe precipitate obtained
  6. filtrationis filtered
  7. washwashed with water
  8. customwith ether to give 810 mg (93%) of crude product 1d
  9. customRecrystallization from the MeOH—H2O pair

Sources & evidence

ORD record
ord-cb03420f548a4b7aacad898bc36713b3
Source dataset
uspto-grants-2006_06
Patent number
US07060441B2

Reaction notes

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