Water → HCID 86606497, compound

HRID 1994126Notes

Reaction equation

HRID 1994126 reaction equation
[OH:1][CH2:2][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[H-].[Na+].[CH3:23]I.O>C1COCC1>[CH3:23][O:1][CH2:2][C@@H:3]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:10])([CH3:11])[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86606496471296-73-8

Product 1

HCID 86606497HCID 86606497, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of di-tert-butyl [(2S)-3-hydroxypropane-1,2-diyl]biscarbamate (2.45 g, 8.10 mmol) in THF (80 mL) at 0° C., was added NaH (60%, 357 mg, 8.91 mmol). The reaction was allowed to stir at 0° C. for 30 min, and then methyl iodide (0.556 mL, 8.91 mmol) was added dropwise. The reaction was stirred at 0° C. for 1 h and then allowed to warm to rt and stirred for 3 h. Water was added and the reaction was extracted into EtOAc. The combined organic solutions were washed with brine, dried (Na2SO4) and evaporated. The residue was purified by chromatography (SiO2, EtOAc/hexane) to yield the title compound as a white solid (895 mg, 36%).

Workup

  1. stirringThe reaction was stirred at 0° C. for 1 h
  2. temperatureto warm to rt
  3. stirringstirred for 3 h
  4. extractionthe reaction was extracted into EtOAc
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customThe residue was purified by chromatography (SiO2, EtOAc/hexane)

Sources & evidence

ORD record
ord-ee55feace5ac4ee39d56176525e8efc7
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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