Triethylamine → HCID 87326558, compound

HRID 2170749Notes

Reaction equation

HRID 2170749 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][CH:7]2[C:11]([CH2:13][N:14]3[CH:18]=[N:17][CH:16]=[N:15]3)([OH:12])[C:10]([CH2:21][OH:22])([CH2:19][OH:20])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[S:32](Cl)([CH3:35])(=[O:34])=[O:33]>COCCOC>[CH3:35][S:32]([O:22][CH2:21][C:10]1([CH2:19][O:20][S:32]([CH3:35])(=[O:34])=[O:33])[CH2:9][CH2:8][CH:7]([CH2:6][C:5]2[CH:23]=[CH:24][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:11]1([OH:12])[CH2:13][N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)(=[O:34])=[O:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67255453HCID 67255453, compound2×

Product 1

HCID 87326558HCID 87326558, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

5-(4-chlorobenzyl)-2,2-bis(hydroxymethyl)-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol (0.50 g, 1.42 mmol) (Compound (4)) and triethyl amine (0.70 ml, 1.42×3.5 mmol) were dissolved in DME (15 ml). After adding mesyl chloride (0.30 ml, 1.42×2.7 mmol) under ice-cooling, the solution was removed from the ice bath and stirred for 5 hours at room temperature. After the stirring was complete, 1N aqueous solution of hydrochloric acid was added and then extracted using ethyl acetate. After washing the organic layer using a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, the organic layer was dried using anhydrous sodium sulfate and then concentrated. The concentrate was refined using a silica gel column to obtain white, viscous Compound (3).

Workup

  1. temperaturecooling
  2. customthe solution was removed from the ice bath
  3. addition1N aqueous solution of hydrochloric acid was added
  4. extractionextracted
  5. washAfter washing the organic layer
  6. dry with materiala saturated aqueous solution of sodium chloride, the organic layer was dried
  7. concentrationconcentrated
  8. customto obtain white

Sources & evidence

ORD record
ord-dd2bc2750ca941be87196641815d4c21
Source dataset
uspto-grants-2015_06
Patent number
US09051298B2

Reaction notes

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