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Dimethyl Sulfoxide → (E)-3-[(2S,4S)-N-Allyloxycarbonyl-4-mercaptopyrrolidin-2-yl]-N,N-dimethylacrylamide

HRID 2371828
Notes
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Reaction equation

HRID 2371828 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:9][C@H:8]1[CH2:32]O)=[O:6])[CH:2]=[CH2:3].CS(C)=O.C(OP([CH:46]1C[CH2:49][NH:48][C:47]1=[O:51])(OCC)=O)C.[C:52](Cl)(=O)C(Cl)=O.[H-].[Na+]>>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([SH:12])[CH2:9][C@H:8]1/[CH:32]=[CH:46]/[C:47]([N:48]([CH3:52])[CH3:49])=[O:51])=[O:6])[CH:2]=[CH2:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 10551897(2S,4S)-N-allyloxycarbonyl-2-hydroxymethyl-4-tritylthiopyrrolidineHCID 88508163Oxalyl chloride 3-(diethylphosphono)-2-oxopyrrolidine

Product 1

HCID 86745545(E)-3-[(2S,4S)-N-Allyloxycarbonyl-4-mercaptopyrrolidin-2-yl]-N,N-dimethylacrylamideYield 21.4%

Procedure

The same operation as in Reference Example 4-1) was carried out by using (2S,4S)-N-allyloxycarbonyl-2-hydroxymethyl-4-tritylthiopyrrolidine (the compound obtained in Reference Example 3-1); 11.12 g, 24.2 mmol), dimethyl sulfoxide (4.81 ml, 67.7 mmol), oxalyl chloride 3-(diethylphosphono)-2-oxopyrrolidine (5.35 g, 24.2 mmol) and 60% sodium hydride (870 mg, 21.8 mmol), followed by flash column chromatographic purification on silica gel (Wakogel® C-300, 100 ml, elution with hexane-ethyl acetate 1:1 - ethyl acetate) to give the title compounds ((Z)-form 2.72 g, 21.4% yield; (E)-form 5.15 g, 40.6 % yield).

Workup

  1. customobtained in Reference Example 3-1)

Sources & evidence

ORD record
ord-71054ad1cebf418893e350e8d61ef272
Source dataset
uspto-grants-1992_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05095013

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes