Dimethyl Sulfoxide → HCID 86739365, compound

HRID 325982Notes

Reaction equation

HRID 325982 reaction equation
[S:1]([O:11][CH2:12][C:13]1([CH2:35][O:36][S:37]([C:40]2[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=2)(=[O:39])=[O:38])[CH2:26][C@@H:25]2[C@:16]34[CH2:29][CH2:28][N:27]([CH3:30])[C@@H:24]2[CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:31][CH3:32])=[C:18]([O:33][C@H:15]3[C@@H:14]1[OH:34])[C:17]4=2)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CS(C)=O.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[S:37]([O:36][CH2:35][C:13]1([CH2:12][O:11][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:2])=[O:3])[CH2:26][C@@H:25]2[C@:16]34[CH2:29][CH2:28][N:27]([CH3:30])[C@@H:24]2[CH2:23][C:22]2[CH:21]=[CH:20][C:19]([O:31][CH3:32])=[C:18]([O:33][C@H:15]3[C:14]1=[O:34])[C:17]4=2)([C:40]1[CH:41]=[CH:42][C:43]([CH3:44])=[CH:45][CH:46]=1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9845Trifluoroacetic anhydrideHCID 13020702HCID 13020702, compound

Product 1

HCID 86739365HCID 86739365, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of crude 2 (66.6 g, 99.4 mmole) in CH2Cl2 (250 mL) was added dropwise under argon to a mixture prepared from DMSO (14.2 mL, 200 mmole) in CH2Cl2 (100 mL) and TFAA (21.2 mL, 150 mmole) in CH2Cl2 (70 mL) as reported above for 6. The mixture was stirred in the dry ice acetone bath for 90 min. TEA (40 mL) was added and the mixture then allowed to warm to room temperature. The solution was evaporated, the residue dissolved in CHCl3 and washed 3 times with dilute NH4OH. Evaporation of the dried organic phase gave a foam which crystallized from 95% ethanol to give 53.8 g (81%) of 10 as white crystals, mp 150°-153° C. Recrystallization from 95% ethanol gave analytically pure 10, mp 155°-156° C.; NMR δ 7.2-7.9 (m, 811, tosyl 11's); 7.70 (s, 2H, H1 and H2); 4.47 (s, H5).

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue dissolved in CHCl3
  3. washwashed 3 times with dilute NH4OH
  4. customEvaporation of the dried organic phase
  5. customgave a foam which
  6. customcrystallized from 95% ethanol

Sources & evidence

ORD record
ord-8272287a75204b9d938976e29b113d76
Source dataset
uspto-grants-1984_04
Patent number
US04443605

Reaction notes

Loading…