Triethylamine → HCID 66839529, compound

HRID 546687Notes

Reaction equation

HRID 546687 reaction equation
C(N(CC)CC)C.CS([Cl:12])(=O)=O.O[CH2:14][CH2:15][C@@H:16]([O:38][CH2:39][O:40][CH3:41])[C@H:17]([C:29]1[CH:34]=[C:33]([F:35])[C:32]([F:36])=[C:31]([F:37])[CH:30]=1)[C:18]([NH:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19].O.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[Cl:12][CH2:14][CH2:15][C@@H:16]([O:38][CH2:39][O:40][CH3:41])[C@H:17]([C:29]1[CH:34]=[C:33]([F:35])[C:32]([F:36])=[C:31]([F:37])[CH:30]=1)[C:18]([NH:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66839103HCID 66839103, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66839529HCID 66839529, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.209 mL) and methanesulfonyl chloride (58 uL) were added to a solution of tert-butyl N′-[(2S*,3R*)-5-hydroxy-3-methoxymethoxy-2-(3,4,5-trifluorophenyl)pentanoyl]hydrazinecarboxylate (264 mg) in methylene chloride (10 mL) at 0° C. The reaction solution was stirred at 0° C. for 30 minutes. Then, ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. Subsequently, lithium chloride (265 mg) was added to a solution of the residue in DMF (5 mL), and the reaction solution was stirred at 80° C. for three hours. The reaction solution was left to cool to room temperature. Then, water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 87.5 mg of the title compound. The property value of the compound is as follows.

Workup

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionSubsequently, lithium chloride (265 mg) was added to a solution of the residue in DMF (5 mL)
  6. stirringthe reaction solution was stirred at 80° C. for three hours
  7. waitThe reaction solution was left
  8. temperatureto cool to room temperature
  9. additionThen, water and ethyl acetate were added to the reaction solution
  10. customthe organic layer was separated
  11. washThe resulting organic layer was washed with brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

Sources & evidence

ORD record
ord-554ac18ffe004162ba599e29c0a17d68
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

Loading…