Dimethyl Sulfoxide → HCID 57148713, compound

HRID 2298105Notes

Reaction equation

HRID 2298105 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:32])[CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]2)=[CH:14][C:13]=1[C:33]([NH:35][CH2:36][C:37]12[CH2:46][CH:41]3[CH2:42][CH:43]([CH2:45][CH:39]([CH2:40]3)[CH2:38]1)[CH2:44]2)=[O:34].C(N(CC)CC)C>ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:21][CH2:20]2)=[O:32])=[CH:14][C:13]=1[C:33]([NH:35][CH2:36][C:37]12[CH2:38][CH:39]3[CH2:40][CH:41]([CH2:42][CH:43]([CH2:45]3)[CH2:44]1)[CH2:46]2)=[O:34]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57254189HCID 57254189, compound

Product 1

HCID 57148713HCID 57148713, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To dimethyl sulphoxide (0.155 ml) in anhydrous dichloromethane (11 ml) at −78° C. was added oxalyl chloride (0.086 ml) and the mixture was stirred for 5min. at −78° C. A solution of 4-[[4-chloro-3-[[(tricyclo[3.3.1.13,7]dec-1-ylmethyl)amino]carbonyl]phenyl]hydroxymethyl]-1-piperidinecarboxylic acid, 1,1-dimethylethyl ester (0.47 g, Example 64) in anhydrous dichloromethane (3 ml) was added dropwise and the mixture was stirred for 15 min. at −78° C. Triethylamine (0.633 ml) was then added and the solution was warmed to room temperature. After 45 min. at room temperature, the reaction mixture was poured onto water and the layers were separated. The organic extract was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by HPLC eluting a gradient of 0-5% ethanol in dichloromethane to give the subtitle compound as a white foam (0.31 g).

Workup

  1. stirringthe mixture was stirred for 15 min. at −78° C
  2. temperaturethe solution was warmed to room temperature
  3. waitAfter 45 min. at room temperature
  4. additionthe reaction mixture was poured onto water
  5. customthe layers were separated
  6. extractionThe organic extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by HPLC
  11. washeluting a gradient of 0-5% ethanol in dichloromethane

Sources & evidence

ORD record
ord-6064b44a0ace40f9adf995d51e091e86
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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