Dimethyl Sulfoxide → HCID 86693765, compound

HRID 245050Notes

Reaction equation

HRID 245050 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([N:18]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C@H:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[OH:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>ClCCl>[CH2:25]([N:18]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C@H:19]1[CH2:23][CH2:22][CH2:21][C:20]1=[O:24])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 86693766HCID 86693766, compound

Product 1

HCID 86693765HCID 86693765, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-60 °C

Procedure

To a solution of oxalyl chloride (6.28 mL, 72.4 mmol) in dichloromethane (75 mL) at −60° C. under nitrogen is added a solution of DMSO (10.7 mL, 151 mmol) in dichloromethane (75 mL) dropwise and stirred at −60° C. for 15 min. (1R,2S)-2-(dibenzylamino)cyclopentanol (17.0 g, 60 mmol) in dichloromethane (75 mL) is added and the reaction is stirred at −60° C. for 30 min. TEA (46 mL, 330 mmol) is added and the reaction is allowed to warm to room temperature and stirred for 1 h. Water is added (100 mL) and the reaction is stirred overnight. The dichloromethane layer is separated, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound as an orange oil (13.96 g, 83%). ES/MS m/z 280 (M+1).

Workup

  1. additionis added
  2. temperatureto warm to room temperature
  3. stirringstirred for 1 h
  4. stirringthe reaction is stirred overnight
  5. customThe dichloromethane layer is separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b48a71b565a43f4993e04a449a2e38d
Source dataset
uspto-grants-2014_02
Patent number
US08658693B2

Reaction notes

Loading…