Dimethyl Sulfoxide → HCID 14994957, compound

HRID 129495Notes

Reaction equation

HRID 129495 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([C:13]([CH3:25])([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]1)=[O:17])[CH3:14])#[N:12].C(N(CC)CC)C>ClCCl>[C:11]([C:13]([CH3:25])([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20][CH2:19]1)=[O:17])[CH3:14])#[N:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14994956HCID 14994956, compound

Product 1

HCID 14994957HCID 14994957, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5.06 ml of dimethylsulfoxide was gradually dropped, at -78° C. into a solution of 4.15 ml of oxalyl chloride in dichloromethane (50 ml), into which a dichloromethane solution of 5.05 g of 1-(1-cyano-1-methylethoxycarbonyl)-4-hydroxypiperidine was dropped. After agitation at the temperature for 1 hour, 16.57 ml of triethylamine was added, followed by agitation at room temperature for 1 hour. The reaction solution was filtered, washed with water, and dried with anhydrous magnesium sulfate. The solvent was distilled off and the resultant residue was purified by silica gel column chromatography (elution solvent: ethyl acetate:n-hexane=1:9), thereby obtaining 3.9 g of the intended compound.

Workup

  1. additionwas dropped
  2. waitfollowed by agitation at room temperature for 1 hour
  3. filtrationThe reaction solution was filtered
  4. washwashed with water
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe resultant residue was purified by silica gel column chromatography (elution solvent: ethyl acetate:n-hexane=1:9)

Sources & evidence

ORD record
ord-9f8e455933474ebaaceb49ec21d5a692
Source dataset
uspto-grants-1995_11
Patent number
US05468740

Reaction notes

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