Dimethyl Sulfoxide → HCID 15381154, compound

HRID 1740495Notes

Reaction equation

HRID 1740495 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][C:13]1[CH:30]=[CH:29][C:16]2[C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][O:26][CH3:27])[O:22][C:21]3=[O:28])=[CH:18][O:19][C:15]=2[CH:14]=1.C(N(CC)CC)C>ClCCl.O>[CH:12]([C:13]1[CH:30]=[CH:29][C:16]2[C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][O:26][CH3:27])[O:22][C:21]3=[O:28])=[CH:18][O:19][C:15]=2[CH:14]=1)=[O:11]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15381153HCID 15381153, compound

Product 1

HCID 15381154HCID 15381154, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

1 ml (14.4 mmol) of dimethyl sulphoxide in 20 ml of dichloromethane is added to a solution, cooled to -70° C., of 0.75 ml (8.6 mmol) of oxalyl chloride in 20 ml of dichloromethane. The mixture is stirred for 15 min and a solution of 2.0 g (7.2 mmol) of (R)-3-[6-(hydroxymethyl)benzofuran-3-yl]-5-(methoxymethyl)oxazolidin-2-one in 35 ml of dichloromethane is slowly added. The mixture is stirred for three hours at -70° C. and 5.0 ml (36 mmol) of triethylamine are added. After returning to room temperature, the mixture is poured into 50 ml of water, the product is extracted with dichloromethane and the organic phase is dried over sodium sulphate and concentrated under reduced pressure. The product is purified by chromatography on silica gel and an oil is recovered which is crystallized from ethyl ether.

Workup

  1. stirringThe mixture is stirred for three hours at -70° C.
  2. customAfter returning to room temperature
  3. extractionthe product is extracted with dichloromethane
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe product is purified by chromatography on silica gel
  7. customan oil is recovered which
  8. customis crystallized from ethyl ether

Sources & evidence

ORD record
ord-c76e14a046dc499cba9883c910e11c1e
Source dataset
uspto-grants-1999_10
Patent number
US05969146

Reaction notes

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