Sodium Carbonate → HCID 22708209, compound

HRID 353197Notes

Reaction equation

HRID 353197 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=O)[CH2:11][N:12]([CH2:19][C:20]1[CH:36]=[CH:35][C:23]([O:24][C:25]([CH3:34])([CH3:33])[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:22][CH:21]=1)[CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1.B.CSC.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][N:12]([CH2:19][C:20]1[CH:21]=[CH:22][C:23]([O:24][C:25]([CH3:34])([CH3:33])[C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])=[CH:35][CH:36]=1)[CH2:13][C:14]1[O:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 22708223HCID 22708223, compound

Product 1

HCID 22708209HCID 22708209, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml toluene, 0.25 g (0.50 mmol) of the compound from Example 3-1 is treated with 0.30 ml of 2 M borane-dimethyl sulphide solution in tetrahydrofuran, and the mixture is heated at the boil for 2 hours. The mixture is then stirred in the presence of 5 ml of 2 N sodium carbonate solution for 1 hour and the organic phase is washed with water and with saturated sodium chloride solution. The organic phase is dried over magnesium sulphate and the solvent is distilled off, and the residue is then purified using silica gel flash chromatography (cyclohexane/dichloromethane 3:1→cyclohexane/ethyl acetate 10:1). This gives the target compound in a yield of 37%.

Workup

  1. temperaturethe mixture is heated at the boil for 2 hours
  2. washthe organic phase is washed with water and with saturated sodium chloride solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. distillationthe solvent is distilled off
  5. customthe residue is then purified
  6. customThis gives the target compound in a yield of 37%

Sources & evidence

ORD record
ord-66184823d9704f358704dd67297c1864
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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