Dimethyl Sulfoxide → HCID 10961270, compound

HRID 1590108Notes

Reaction equation

HRID 1590108 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:40]=[CH:39][C:15]([CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([OH:26])=[CH:23][CH:24]=3)[C:19]([S:27][CH2:28][CH2:29][OH:30])=[C:18]2[CH2:31][C:32]([CH3:38])([CH3:37])[C:33]([O:35][CH3:36])=[O:34])=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][N:17]2[C:25]3[C:20](=[CH:21][C:22]([OH:26])=[CH:23][CH:24]=3)[C:19]([S:27][CH2:28][CH:29]=[O:30])=[C:18]2[CH2:31][C:32]([CH3:38])([CH3:37])[C:33]([O:35][CH3:36])=[O:34])=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14980569HCID 14980569, compound

Product 1

HCID 10961270HCID 10961270, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (579 mg, 4.56 mmol) in CH2Cl2 (15 mL) at -70° C. there was slowly added DMSO (711 mg, 9.12 mmol). The mixture was stirred for 3 minutes, then at -70° C. there was slowly added a solution of the alcohol from Step 5 (1.7 g, 3.8 mmol) in CH2Cl2 (15 mL). The resulting mixture was stirred at -70° C. for 20 minutes, then there was slowly added Et3N (1.92 g, 19 mmol). The mixture was stirred in the cold for a further 5 minutes, then it was allowed to warm up to room temperature. After dilution with Et2O (200 mL) the mixture was washed twice with 1N HCl, then with H2O (3×), dried and evaporated to a residue which was chromatographed on silica gel, eluting with a 1:1 mixture of hexane and EtOAc, to afford the title compound as a thick oil.

Workup

  1. customat -70° C.
  2. stirringThe resulting mixture was stirred at -70° C. for 20 minutes
  3. stirringThe mixture was stirred in the cold for a further 5 minutes
  4. washAfter dilution with Et2O (200 mL) the mixture was washed twice with 1N HCl
  5. dry with materialwith H2O (3×), dried
  6. customevaporated to a residue which
  7. customwas chromatographed on silica gel
  8. washeluting with a 1:1 mixture of hexane and EtOAc

Sources & evidence

ORD record
ord-6be6fe4ff3214b5b8adc79749b424e65
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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