Sodium hydride → HCID 69130062, compound

HRID 915647Notes

Reaction equation

HRID 915647 reaction equation
[H-].[Na+].C(OC(=O)[NH:9][CH2:10][CH2:11][SH:12])(C)(C)C.[F:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](F)[N:16]=1>O1CCCC1.C(Cl)Cl>[F:14][C:15]1[N:16]=[C:17]([S:12][CH2:11][CH2:10][NH2:9])[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 739342,6-DifluoropyridineHCID 3017761N-(tert-butoxycarbonyl)-2-aminoethanethiol

Product 1

HCID 69130062HCID 69130062, compoundYield 127.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Suspend sodium hydride (138 mg, 5.46 mmol) in tetrahydrofuran (6 mL) and cool to 0° C. in an ice bath. Add (2-mercaptoethyl)carbamic acid tert-butyl ester (0.461 mL, 2.73 mmol) dropwise over 5 minutes. Stir reaction for 30 minutes, add 2,6-difluoropyridine (0.495 mL, 0.546 mmol), remove ice bath and stir an additional hour. Re-cool reaction and quench with water. Extract with 1/1 hexanes/ethyl acetate. Dry organics over magnesium sulfate, filter and evaporate. Perform flash column chromatography (ethyl acetate/hexanes). Dissolve resulting orange oil in trifluoroacetic acid (3 mL) and stir for 15 minutes. Concentrate the reaction with a stream of dry nitrogen, re-dissolve in dry methylene chloride and evaporate to give 120 mg of the title compound as an orange oil. 1H NMR (d MeOH): 7.70 (m, 1H), 7.22 (m, 1H), 6.78 (m, 1H), 3.44 (m, 2H), 3.34 (m, 2H).

Workup

  1. customreaction for 30 minutes
  2. customremove ice bath
  3. stirringstir an additional hour
  4. customRe-cool reaction
  5. customquench with water
  6. extractionExtract with 1/1 hexanes/ethyl acetate
  7. filtrationDry organics over magnesium sulfate, filter
  8. customevaporate
  9. dissolutionDissolve
  10. customresulting orange oil in trifluoroacetic acid (3 mL)
  11. stirringstir for 15 minutes
  12. concentrationConcentrate
  13. customthe reaction with a stream of dry nitrogen
  14. customevaporate

Sources & evidence

ORD record
ord-cb09827266f14c369a2696c26aea7074
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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