Dimethyl Sulfoxide → HCID 86584831, compound

HRID 458324Notes

Reaction equation

HRID 458324 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([S:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH2:20][C@H:19]1[CH2:33][OH:34])=[O:17])([CH3:14])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:22][C@H:21]([S:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH2:20][C@H:19]1[CH:33]=[O:34])=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 69432327HCID 69432327, compound

Product 1

HCID 86584831HCID 86584831, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To 4.2 ml (48.65 mmol, 1.2 eq) oxalyl chloride in 100 ml CH2Cl2 were added 6.5 ml (89.19 mmol, 2.2 eq) DMSO in 20 ml CH2Cl2 at −65° C., followed after 10 min by 14.33 g (40.54 mmol, 1.0 eq) (2S,4R)-2-hydroxymethyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester in 60 ml CH2Cl2 over a period of 20 min. The solution was stirred at −68° C. for 1.5 h before 28 ml (162.16 mmol, 4 eq) iPr2NEt were added, and the reaction mixture was warmed to room temperature. The solution was extracted with 1M KHSO4, the combined inorganic phases were extracted with CH2Cl2 and the organic phase dried over Na2SO4 and evaporated, yielding 14.18 g (99%) (2S,4R)-2-formyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester. The crude product was subjected to the following reaction without further purification.

Workup

  1. additionwere added
  2. extractionThe solution was extracted with 1M KHSO4
  3. extractionthe combined inorganic phases were extracted with CH2Cl2
  4. dry with materialthe organic phase dried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-54b4e20f0565414abb00c25dd2d838fd
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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