Dimethyl Sulfoxide → HCID 23383852, compound

HRID 1281997Notes

Reaction equation

HRID 1281997 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:13]=1[CH2:14][N:15]1[CH2:19][C@H:18]([C:20]2[CH:24]=[CH:23][S:22][CH:21]=2)[C@@H:17]([CH2:25][OH:26])[CH2:16]1.CCOCC>C(Cl)Cl>[Cl:11][C:12]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:13]=1[CH2:14][N:15]1[CH2:19][C@H:18]([C:20]2[CH:24]=[CH:23][S:22][CH:21]=2)[C@@H:17]([CH:25]=[O:26])[CH2:16]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 65578Oxalyl chlorideHCID 23383853HCID 23383853, compound

Product 1

HCID 23383852HCID 23383852, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.31 mL (3.6 mmol) of oxalyl chloride in 20 mL of CH2Cl2 at −78° C. was added 0.51 mL (7.2 mmol) of DMSO and the reaction mixture was stirred. After 10 min., a solution of 0.49 g (1.8 mmol) of 1-(2,4-dichlorobenzyl)-3-(R)-hydroxymethyl-4-(S)-(3-thienyl)pyrrolidine in 20 mL of CH2Cl2 was then added. After stirring for 10 min. at −78° C., the reaction was allowed to warm to rt. The reaction mixture was poured into ether and extracted twice with sat'd NaHCO3 solution and once with sat'd NaCl solution. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated to give 0.49 g of the title compound. Mass Spectrum (ESI) m/e=340 (M+1 35Cl, 35Cl), 342 (M+1 35Cl, 37Cl), and 344 (M+1 37Cl, 37Cl).

Workup

  1. stirringAfter stirring for 10 min. at −78° C.
  2. extractionextracted twice with sat'd NaHCO3 solution and once with sat'd NaCl solution
  3. dry with materialThe organic fraction was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a3ede8df51d14f4bac01a94798f1e0a2
Source dataset
uspto-grants-2002_09
Patent number
US06455548B2

Reaction notes

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