Dimethyl Sulfoxide → HCID 22882481, compound

HRID 863293Notes

Reaction equation

HRID 863293 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16]([N:18]1[C@@H:22]([CH2:23][C:24]2([CH2:27][OH:28])[CH2:26][CH2:25]2)[CH2:21][O:20][C:19]1([CH3:30])[CH3:29])=[O:17])([CH3:14])([CH3:13])[CH3:12].S([O-])(O)(=O)=O.[K+]>C(Cl)Cl.C(N(CC)CC)C>[C:11]([O:15][C:16]([N:18]1[C@@H:22]([CH2:23][C:24]2([CH:27]=[O:28])[CH2:26][CH2:25]2)[CH2:21][O:20][C:19]1([CH3:30])[CH3:29])=[O:17])([CH3:13])([CH3:14])[CH3:12]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 516920Potassium bisulfateHCID 22882482HCID 22882482, compound

Product 1

HCID 22882481HCID 22882481, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

11.1 ml of dimethylsulfoxide in 150 ml of methylene chloride are added dropwise to a solution of 10.1 ml of oxalyl chloride in 130 ml of methylene chloride at -60° C. When the addition has ended, the mixture is subsequently stirred for a further 10 min, a solution of 22.3 g of 3-tert-butoxycarbonyl-2,2-dimethyl-4(S)-[(1-hydroxymethylcyclopropyl)methyl]-1,3-oxazolidine in 270 ml of methylene chloride is then added at -60° C. in the course of 20 min and the mixture is stirred for a further 30 min. 43.6 ml of triethylamine are then added at the same temperature and finally, after 30 min, 140 ml of a 20% potassium hydrogen sulfate solution are added to the reaction mixture. Customary working up gives the title compound as a crude product: Rf (A)=0.73.

Workup

  1. additionWhen the addition
  2. stirringthe mixture is stirred for a further 30 min
  3. waitfinally, after 30 min

Sources & evidence

ORD record
ord-746197a5e39d4f869dd0e952ff5282d4
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

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