Dimethyl Sulfoxide → HCID 59200366, compound

HRID 1685329Notes

Reaction equation

HRID 1685329 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][C:13]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>ClCCl.Cl>[O:11]=[CH:12][C:13]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH2:14][NH:15][C:16](=[O:25])[O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59200464HCID 59200464, compound

Product 1

HCID 59200366HCID 59200366, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of oxalyl chloride (5.39 mL, 61.53 mmol) in dichloromethane (100 mL) was added dropwise dry DMSO (6.83 mL, 96.15 mmol) at −78° C. After 10 minutes at this temperature, a solution of benzyl 3-hydroxy-2,2-diphenylpropylcarbamate (13.9 g, 38.46 mmol) in dichloromethane (100 mL) was slowly added and stirred at −78° C. The reaction was stirred for 1 hour and triethylamine (26.8 mL, 192.3 mmol) was added and the reaction stirred at −78° C. for 10 more minutes then warmed to room 23° C. The reaction was diluted with 1N HCl and the phases were separated. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude title material (12.09 g, 87%) as an oil which was used as such in the next reaction. HPLC ret. time (Condition A): 2.093 min. LC/MS (M+H)+: 360. 1H NMR (400 MHz, CDCl3) δ ppm: 4.18 (2H, d, J=6.57 Hz), 4.98 (2H, s), 5.00 (1H, t, J=5.81 Hz), 7.17-7.42 (15H, 2 m), 9.90 (1H, s).

Workup

  1. stirringThe reaction was stirred for 1 hour
  2. stirringthe reaction stirred at −78° C. for 10 more minutes
  3. temperaturethen warmed to room 23° C
  4. customthe phases were separated
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b83366e13dcc4de98a56f624084f8856
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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