Dimethyl Sulfoxide → HCID 59017212, compound

HRID 969270Notes

Reaction equation

HRID 969270 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][C@H:12]1[CH2:21][N:20]2[C@H:14]([CH2:15][O:16][C:17]3[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=3[C:19]2=[O:22])[CH2:13]1.C(N(CC)CC)C>ClCCl.O.C(OCC)(=O)C>[O:11]=[C:12]1[CH2:21][N:20]2[C@H:14]([CH2:15][O:16][C:17]3[CH:26]=[CH:25][CH:24]=[CH:23][C:18]=3[C:19]2=[O:22])[CH2:13]1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59017210HCID 59017210, compound

Product 1

HCID 59017212HCID 59017212, compoundYield 22.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of oxalyl chloride (0.52 ml; 5.94 mmol) in dry dichloromethane (15 ml) cooled to −78° C. was added a solution of dimethylsulfoxide (0.81 ml, 11.42 mmol) in dry dichloromethane (2 ml). Stirring was continued for 10 minutes followed by dropwise addition of a solution of the material (1 g) prepared in Example 25 (4.57 mmol) in dry dichloromethane (10 ml). The mixture was stirred for a further 15 minutes then triethylamine (3.8 ml; 27.3 mmol) was added. After stirring at −78° C. for a further 10 minutes the mixture was allowed to warm to 0° C. before ethyl acetate (50 ml) and water (50 ml) were added. After thorough mixing the organic layer was separated, washed sequentially with 1M HCl (50 ml) and brine (50 ml), and dried (Na2SO4). The solvent was removed under reduced pressure and the residue purified by flash chromatography eluting with 3% MeOH in methylene chloride to give the title product (220 mg) which was recrystallised once from the minimum of hot ethyl acetate, 1H NMR (CDCl3) δ 2.41 (dd, 1H), 2.87-2.93 (m, 1H), 4.15-4.33 (m, 3H), 4.45-4.49 (m, 2H), 7.06 (d, 1H), 7.18 (t, 1H), 7.44 (dd, 1H), 8.03 (dd, 1H); EIMS: m/z =218.4 [M+H]+

Workup

  1. stirringThe mixture was stirred for a further 15 minutes
  2. stirringAfter stirring at −78° C. for a further 10 minutes the mixture
  3. additionwere added
  4. additionAfter thorough mixing the organic layer
  5. customwas separated
  6. washwashed sequentially with 1M HCl (50 ml) and brine (50 ml)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was removed under reduced pressure
  9. customthe residue purified by flash chromatography
  10. washeluting with 3% MeOH in methylene chloride

Sources & evidence

ORD record
ord-0c4d406df3fa4fbc800672b614256f30
Source dataset
uspto-grants-2007_12
Patent number
US07307073B2

Reaction notes

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