Dimethyl Sulfoxide → HCID 58124943, compound

HRID 1971716Notes

Reaction equation

HRID 1971716 reaction equation
[C:1]([N:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].CS(C)=O.C(N(CC)CC)C.N1C(=O)CC[C@H]1C(O)=O>ClCCl.CCCCCCC.C(OCC)(=O)C>[C:1]([N:5]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]=[O:19])[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7405L-Pyroglutamic AcidHCID 8471TriethylamineHCID 58124868HCID 58124868, compound

Product 1

HCID 58124943HCID 58124943, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

A solution of 1.1 g of 16f, in a mixture of 30 ml of dichloromethane, 15 ml of DMSO and 3 ml of triethyl amine, was treated with 1 g of Pyr.SO3 at 0° C. The reaction mixture was then stirred at RT for 2 hr. The mixture was partially concentrated and poured into water and the product was extracted with diethyl ether. The organic extract was washed with water, dried, concentrated and the crude material was purified by passing through a short silica column, to give 1.1 g of crude product, which was passed through silica gel, using a gradient of heptane/ethyl acetate as eluent, to provide 0.85 g of 16g as a colorless oil.

Workup

  1. customat 0° C
  2. concentrationThe mixture was partially concentrated
  3. additionpoured into water
  4. extractionthe product was extracted with diethyl ether
  5. extractionThe organic extract
  6. washwas washed with water
  7. customdried
  8. concentrationconcentrated
  9. customthe crude material was purified
  10. customto give 1.1 g of crude product, which

Sources & evidence

ORD record
ord-4e6e6e8dfc504aabad3cf6499580720d
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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