Benzoic Acid → HCID 88179647, compound

HRID 1018911Notes

Reaction equation

HRID 1018911 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:22]([O:24][P:25]([C:30]1[C:31](=[O:45])[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([S:40]([NH2:43])(=[O:42])=[O:41])=[C:35]([Cl:44])[CH:34]=2)(=[O:29])[O:26][CH2:27][CH3:28])[CH3:23].C1CCN2C(=NCCC2)CC1.Cl>C1COCC1>[CH2:27]([O:26][P:25]([C:30]1[C:31](=[O:45])[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([S:40]([NH:43][C:1](=[O:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)(=[O:41])=[O:42])=[C:35]([Cl:44])[CH:34]=2)(=[O:29])[O:24][CH2:22][CH3:23])[CH3:28]

Participants

7

Reactant 5

HCID 243Benzoic Acid2×HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 88064075HCID 88064075, compound

Product 1

HCID 88179647HCID 88179647, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of benzoic acid (111 mg, 0.912 mmol) in 3 ml of anhydrous THF containing 173 mg (1.06 mmol) of carbonyldiimidazole is stirred for 45 minutes at reflux. In parallel, there is prepared a suspension of 300 mg (0.760 mmol) of the compound obtained in Step A in 3 ml of THF, to which there is added 0.125 ml (0.836 mmol) of DBU. Stirring is carried out for 15 minutes at room temperature, and then the benzoic acid solution prepared above is added thereto. The mixture is heated for 3 hours at 60° C. The reaction mixture is cooled in an ice bath and rendered acidic by the addition of 1N HCl. Extraction is carried out with ethyl acetate. The organic phases are combined and washed with a saturated NaCl solution and then dried over MgSO4. After evaporation, the residue is chromatographed over a silica column whilst eluting with a gradient (95/5-90/10) of CH2Cl2/MeOH. The title product is obtained in the form of a white solid.

Workup

  1. temperatureat reflux
  2. customIn parallel, there is prepared
  3. additionabove is added
  4. temperatureThe reaction mixture is cooled in an ice bath
  5. extractionExtraction
  6. washwashed with a saturated NaCl solution
  7. dry with materialdried over MgSO4
  8. customAfter evaporation
  9. customthe residue is chromatographed over a silica column
  10. washwhilst eluting with a gradient (95/5-90/10) of CH2Cl2/MeOH

Sources & evidence

ORD record
ord-abfa6026b39946bab2547e2123a146e2
Source dataset
uspto-grants-2002_11
Patent number
US06486143B2

Reaction notes

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