Citric Acid → HCID 22350968, compound

HRID 747531Notes

Reaction equation

HRID 747531 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([CH2:13]CN)=[CH:11][S:10][C:9]1=[N:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[O:26][CH3:27])(=[O:3])[CH3:2].C([N:31](CC)CC)C.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42](Cl)(=[O:44])=[O:43])=[CH:38][CH:37]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([CH2:13][NH:31][S:42]([C:39]2[CH:40]=[CH:41][C:36]([CH3:46])=[CH:37][CH:38]=2)(=[O:44])=[O:43])=[CH:11][S:10][C:9]1=[N:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][C:19]=1[O:26][CH3:27])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 69030047HCID 69030047, compound

Product 1

HCID 22350968HCID 22350968, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (200 mg) obtained in the above (4) and triethylamine (100 mg) were dissolved in tetrahydrofuran (5 ml), and thereto was added p-toluenesulfonyl chloride (117 mg) at room temperature under nitrogen atmosphere. Two hours thereafter, to the reaction mixture was added a 10% aqueous citric acid solution, and the mixture was extracted with chloroform. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [chloroform:methanol (97:32)] to give the title compound (240 mg) as amorphous.

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [chloroform:methanol (97:32)]

Sources & evidence

ORD record
ord-5acb83987bba47bda8e3417a6344f46c
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

Loading…