Dimethyl Sulfoxide → HCID 58681680, compound

HRID 2059562Notes

Reaction equation

HRID 2059562 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:13]=1[CH2:14][O:15][CH2:16][C@H:17]1[O:21][CH:20]([O:22][CH3:23])[C@H:19]([OH:24])[C@@H:18]1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34].C(N(CC)CC)C>C(Cl)Cl.O>[Cl:11][C:12]1[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:13]=1[CH2:14][O:15][CH2:16][C@H:17]1[O:21][CH:20]([O:22][CH3:23])[C:19](=[O:24])[C@@H:18]1[O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 58681695HCID 58681695, compound

Product 1

HCID 58681680HCID 58681680, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent4×

Conditions

Temperature
-78 °C

Procedure

To a cooled solution of oxalyl chloride (2.15 ml, 25.1 mmol, 1.3 equiv.) in DCM (20 ml) at −78° C. is added a solution of DMSO (2.85 ml, 36.5 mmol, 1.9 equiv.) in DCM (30 ml) and stirred at −78° C. for 30 mins. Then a solution of (3R,4S,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-tetrahydrofuran-3-ol I-2 (9.6 g, 18.8 mmol, 1 equiv.) in DCM (50 ml) is added slowly and stirred at −78° C. for about 2 h. After that, triethylamine (15.8 ml, 114 mmol, 6.0 equiv.) is added to the reaction mixture and slowly brought to room temperature and stirred for 1 h. After the reaction is completed, the mixture is diluted with water (100 ml) and DCM (50 ml). The DCM layer is separated and washed with 1 N HCl solution and saturated brine, dried (anhyd Na2SO4), concentrated and purified by flash chromatography (hexane:ethyl acetate=70:30) to give (4R,5R)-5-(2,4-Dichlorobenzyloxymethyl)-4-(2,4-dichlorobenzyloxy)-2-methoxy-dihydrofuran-3-one I-3 as slightly yellow oil.

Workup

  1. stirringstirred at −78° C. for about 2 h
  2. customslowly brought to room temperature
  3. stirringstirred for 1 h
  4. customThe DCM layer is separated
  5. washwashed with 1 N HCl solution and saturated brine
  6. dry with materialdried (anhyd Na2SO4)
  7. concentrationconcentrated
  8. custompurified by flash chromatography (hexane:ethyl acetate=70:30)

Sources & evidence

ORD record
ord-c357324bc76149fb8030c029084899f2
Source dataset
uspto-grants-2012_10
Patent number
US08278282B2

Reaction notes

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