Sodium borohydride → HCID 69982512, compound

HRID 2229265Notes

Reaction equation

HRID 2229265 reaction equation
[Te].[BH4-].[Na+].[CH3:4][O:5][C:6]([C:8]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:10]2([CH2:15][CH2:14][N:13]([C:16](=[O:41])[CH:17]([NH:27][C:28](=[O:40])[C:29]([NH2:39])([CH3:38])[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:12][CH2:11]2)[CH:9]=1)=[O:7].C(Cl)Cl.C(OCC)(=O)C>C(O)C>[CH3:4][O:5][C:6]([CH:8]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:10]2([CH2:15][CH2:14][N:13]([C:16](=[O:41])[CH:17]([NH:27][C:28](=[O:40])[C:29]([NH2:39])([CH3:38])[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])[CH2:18][O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:12][CH2:11]2)[CH2:9]1)=[O:7]

Participants

6

Reactant 4

HCID 4311764Sodium borohydrideHCID 6327182TelluriumHCID 21226138Dichloromethane ethylacetateHCID 69832052HCID 69832052, compound

Product 1

HCID 69982512HCID 69982512, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a suspention of Tellurium (52.6 mg, 0.412 mmol) in ethanol (2.0 ml) was added sodiumborohydride (36.6 mg, 0.99 mmol) and the mixture was refluxed for 10 minutes. A solution of the title compound from Example 3, Step E (100 mg, 0.165 mg) in ethanol (1.0 ml) was cannulated into the reaction mixture at room temperature. The reaction mixture was then stirred over night, filtered and concentrated. The residue was dissolved in ethyl acetate and 1 N KOH was added. The aqueous layer was then extracted with ethyl acetate (3×1 vol). The organic layers were dried over anhydrous sodium sulfate, filtered and concentrated. Flash chromatography (silica gel, methylene chloride/ethyl acetate 2:1) gave the title compound (91 mg, 0.15 mmol) as a clear glass.

Workup

  1. temperaturethe mixture was refluxed for 10 minutes
  2. customwas cannulated into the reaction mixture at room temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. addition1 N KOH was added
  7. extractionThe aqueous layer was then extracted with ethyl acetate (3×1 vol)
  8. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-2667ab2fb45a45ec99af08558c20d09d
Source dataset
uspto-grants-2002_07
Patent number
US06420376B1

Reaction notes

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