Dimethyl Sulfoxide → HCID 86753541, compound

HRID 342298Notes

Reaction equation

HRID 342298 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.O[CH:12]([N:26]1[C@H:29]([CH2:30][C:31]([S:33][C@H:34]2[CH2:38][CH2:37][N:36]([C:39](=[N:41][C:42]([O:44][CH2:45][C:46]3[CH:51]=[CH:50][C:49]([N+:52]([O-:54])=[O:53])=[CH:48][CH:47]=3)=[O:43])[CH3:40])[CH2:35]2)=[O:32])[C@H:28]([C@H:55]([O:57][C:58]([O:60][CH2:61][C:62]2[CH:67]=[CH:66][C:65]([N+:68]([O-:70])=[O:69])=[CH:64][CH:63]=2)=[O:59])[CH3:56])[C:27]1=[O:71])[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=O.C(N(CC)CC)C.P([O-])([O-])([O-])=O>C(Cl)Cl>[N+:52]([C:49]1[CH:50]=[CH:51][C:46]([CH2:45][O:44][C:42]([N:41]=[C:39]([N:36]2[CH2:37][CH2:38][C@H:34]([S:33][C:31]([CH2:30][C@H:29]3[N:26]([CH2:12][CH2:13][O:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=4)[C:27](=[O:71])[C@@H:28]3[C@H:55]([O:57][C:58]([O:60][CH2:61][C:62]3[CH:67]=[CH:66][C:65]([N+:68]([O-:70])=[O:69])=[CH:64][CH:63]=3)=[O:59])[CH3:56])=[O:32])[CH2:35]2)[CH3:40])=[O:43])=[CH:47][CH:48]=1)([O-:54])=[O:53]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 1061PhosphateHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86753542HCID 86753542, compound

Product 1

HCID 86753541HCID 86753541, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

110 mg (0.87 mmole) of oxalyl chloride were dissolved in 5 ml of methylene chloride. To the solution was added 137 mg (1.75 mmole) of dimethyl sulphoxide under a stream of a nitrogen gas at -780° C. The mixture was then stirred for 10 minutes, after which a solution of 500 mg (0.577 mmole) of (3R, 4R)-1-[1-hydroxy-1-(p-nitrobenzyloxycarbonyl)methyl]-4-([(S)-1-[N-(p-nitrobenzyloxycarbonyl)acetimidoyl]pyrrolidin-3-ylthio]carbonylmethyl)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-azetidinone was added to the mixture over 2 minutes. The mixture was stirred for 5 minutes and then 250 mg (2.48 mmole) of triethylamine were added thereto and the mixture was stirred for 15 minutes. About 30 ml of a 0.1M phosphate buffer solution (pH 7.1) was added to the mixture, which was then stirred and extracted with methylene chloride. The extract was dried over anhydrous magnesium sulphate and the solvent was distilled off. The residue was quickly subjected to column chromatography through 10 g of silica gel eluted with 2:1 to 1:1 by volume mixtures of benzene and ethyl acetate, to afford 350 mg (yield 70%) of the title product as an oily substance. Infra-red and nuclear magnetic resonance spectra of the product agreed with those of the product obtained as described in Example 16(a)(iii).

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. stirringthe mixture was stirred for 15 minutes
  3. stirringwas then stirred
  4. extractionextracted with methylene chloride
  5. dry with materialThe extract was dried over anhydrous magnesium sulphate
  6. distillationthe solvent was distilled off
  7. washeluted with 2:1 to 1:1 by volume mixtures of benzene and ethyl acetate

Sources & evidence

ORD record
ord-173db9a8616c4509982da07f953dc4c7
Source dataset
uspto-grants-1999_01
Patent number
US05856556

Reaction notes

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