Dimethyl Sulfoxide → HCID 178484048, compound

HRID 967123Notes

Reaction equation

HRID 967123 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16](=[O:28])[N:17]([CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([CH2:26][OH:27])[CH2:22][CH2:21]1)[CH3:18])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16](=[O:28])[N:17]([CH2:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([CH:26]=[O:27])[CH2:22][CH2:21]1)[CH3:18])([CH3:12])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 178484049HCID 178484049, compound

Product 1

HCID 178484048HCID 178484048, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

0.45 ml of oxalyl chloride in 5.0 ml of dichloromethane were cooled to −78° C.; then, 0.41 g of dimethylsulfoxide in 2.0 ml of dichloromethane were slowly added and the reaction mixture stirred at −78° C. for 10 minutes. Then, 0.680 g (2.64 mmol) trans-(4-hydroxymethyl-cyclohexylmethyl)-methyl-carbamic acid tert-butyl ester dissolved in 5.0 ml of dichloromethane were added and the reaction mixture stirred at −78° C. for 10 minutes. Subsequently, 1.84 ml of triethylamine were added at the same temperature, the reaction mixture stirred 30 minutes at −78° C., warmed to room temperature and stirred for 1 hour. It was then poured into 50 ml of an ice/water mixture and extracted 3 times with 50 ml of dichloromethane. The combined dichloromethane phases were washed with dilute hydrochloric acid, sodium hydrogen carbonate solution and with water, dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 4:1 v/v mixture of dichloromethane and ether as the eluent giving 0.615 g (91.1%) trans-(4-formyl-cyclohexylmethyl)-methyl-carbamic acid tert-butyl ester as colorless amorphous solid, MS: 273 (MNH4+).

Workup

  1. additionwere added
  2. stirringthe reaction mixture stirred at −78° C. for 10 minutes
  3. stirringthe reaction mixture stirred 30 minutes at −78° C.
  4. temperaturewarmed to room temperature
  5. stirringstirred for 1 hour
  6. extractionextracted 3 times with 50 ml of dichloromethane
  7. washThe combined dichloromethane phases were washed with dilute hydrochloric acid, sodium hydrogen carbonate solution and with water
  8. dry with materialdried over magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue formed
  11. customwas chromatographed on silica gel with a 4:1 v/v mixture of dichloromethane and ether as the eluent

Sources & evidence

ORD record
ord-0e2cb582d28649da95723ddacb4fb00b
Source dataset
uspto-grants-2005_10
Patent number
US06953806B2

Reaction notes

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