Dimethyl Sulfoxide → HCID 86652423, compound

HRID 1261850Notes

Reaction equation

HRID 1261850 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[C@@H:23]([CH2:24][OH:25])[CH2:22][O:21][CH2:20][C@@H:19]1[CH2:26][CH:27]=[CH2:28])=[O:17])([CH3:14])([CH3:13])[CH3:12].CCN(CC)CC>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[C@H:23]([CH:24]=[O:25])[CH2:22][O:21][CH2:20][C@@H:19]1[CH2:26][CH:27]=[CH2:28])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 67093162HCID 67093162, compound

Product 1

HCID 86652423HCID 86652423, compoundYield 111.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

Dimethyl sulfoxide (498 mg, 6.38 mmol) was added at −70° C. to a solution of oxalyl chloride (405 mg, 3.19 mmol) in DCM (5 mL), then after 15 min a solution of (3S,5S)-3-allyl-5-hydroxymethyl-morpholine-4-carboxylic acid tert-butyl ester (547 mg, 2.13 mmol) in DCM (3 mL) was added. The reaction mixture was stirred at −70° C. for 30 min, then treated with Et3N (1.29 g, 12.8 mmol), then after 20 min the ice bath was removed. After 30 min the reaction mixture was washed with sat. aq. sodium hydrogencarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to afford the title compound (608 mg) as a light yellow gum, which was directly used in the next step.

Workup

  1. customafter 20 min the ice bath was removed
  2. washAfter 30 min the reaction mixture was washed with sat. aq. sodium hydrogencarbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ba2f7add54cb478692a7d180875a94a1
Source dataset
uspto-grants-2013_06
Patent number
US08471004B2

Reaction notes

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