Dimethyl Sulfoxide → HCID 67065856, compound

HRID 604339Notes

Reaction equation

HRID 604339 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:30]1[CH2:34][CH2:33][C@@H:32]([OH:35])[CH2:31]1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[C:11]([N:30]1[CH2:34][CH2:33][C:32](=[O:35])[CH2:31]1)([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58455161HCID 58455161, compound

Product 1

HCID 67065856HCID 67065856, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

To a stirred solution of anhydrous dichloromethane (35.0 mL) in a 3-necked flask with a thermometer, oxalyl chloride (1.5 mL) was added and the resulting solution was cooled to −60° C. A solution of dimethylsulfoxide (2.6 mL) in dichloromethane (7.5 mL) was added over a period of 10 min, and then (3R)-1-tritylpyrrolidin-3-ol (5.0 g) in dichloromethane (15.0 mL) was added over a period of 10 min. The resulting solution was stirred at −60° C. for 15 min, then triethylamine (10.6 mL) was added over a period of 5 min. After 5 min, the cooling bath was removed and the mixture was allowed to warm to room temperature. Water (45 mL) was added. The mixture was stirred for an additional 30 min and then extracted with dichloromethane. The organic phase was washed with 5% aqueous citric acid solution, dried over anhydrous sodium sulfate, filtered and concentrated to yield the title compound. LC-MS=243.1 (M+1).

Workup

  1. waitAfter 5 min
  2. customthe cooling bath was removed
  3. temperatureto warm to room temperature
  4. additionWater (45 mL) was added
  5. stirringThe mixture was stirred for an additional 30 min
  6. extractionextracted with dichloromethane
  7. washThe organic phase was washed with 5% aqueous citric acid solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e36450ee9c404cef81211f4b6bc6f4e2
Source dataset
uspto-grants-2011_03
Patent number
US07910596B2

Reaction notes

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