Citric Acid → HCID 59749206, compound

HRID 747523Notes

Reaction equation

HRID 747523 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[N:13]([CH2:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][OH:20])[C:12]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)=[CH:11][S:10]2)=[C:4]([O:28][CH3:29])[CH:3]=1.[H-].[Na+].Br[CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35].C(O)(=O)[CH2:40][C:41]([CH2:46]C(O)=O)([C:43](O)=O)[OH:42].[O:52]1CCC[CH2:53]1>>[C:41]([O:42][C:53]([N:17]([CH2:16][CH2:15][CH2:14][N:13]1[C:12]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)=[CH:11][S:10][C:9]1=[N:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=1[O:28][CH3:29])[CH2:18][CH2:19][O:20][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[O:52])([CH3:40])([CH3:43])[CH3:46]

Participants

6

Reactant 5

HCID 311Citric AcidHCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 22350987HCID 22350987, compound

Product 1

HCID 59749206HCID 59749206, compound

Procedure

The compound (1.1 g) obtained in Example 321 (2) was dissolved in tetrahydrofuran (20 ml), and thereto was added portionwise sodium hydride (410 mg, 60% dispersion in oil) in several portions under nitrogen atmosphere in an ice bath, and the mixture was stirred for 30 minutes. To the reaction mixture was added ethyl bromoacetate (0.45 ml), and the mixture was warmed to room temperature, and then stirred for 6 hours. The reaction mixture was poured into a 5% aqueous citric acid solution under ice-cooling, and the mixture was extracted with ethyl acetate. 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 [n-hexane:ethyl acetate (8:2)] to give the title compound (980 mg) as colorless oil.

Workup

  1. stirringstirred for 6 hours
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (8:2)]

Sources & evidence

ORD record
ord-589cbf5f990f4bedb644921c529250f6
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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