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

HRID 2371826Notes

Reaction equation

HRID 2371826 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1[CH2:32]O)=[O:6])[CH:2]=[CH2:3].CS(C)=O.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.C(OP([CH2:59][C:60]([N:62]([CH3:64])[CH3:63])=[O:61])(OCC)=O)C.[H-].[Na+]>>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][C@H:8]1/[CH:32]=[CH:59]/[C:60]([N:62]([CH3:63])[CH3:64])=[O:61])=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 6

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 10551897(2S,4S)-N-allyloxycarbonyl-2-hydroxymethyl-4-tritylthiopyrrolidineHCID 11127903diethyl N,N-dimethylcarbamoylmethylphosphonate

Product 1

HCID 67792648(E)-3-[(2S,4S)-N-Allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]-N,N-dimethylacrylamideYield 88.1%

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); 2.00 g, 4.35 mmol), dimethyl sulfoxide (0.87 ml, 12.2 mmol), oxalyl chloride (0.56 ml, 6.5 mmol), triethylamine (3.03 ml, 21 8 mmol), 2-(diethylphosphono)-N,N-dimethylacetamide (1.17 g, 5.22 mmol) and 60% sodium hydride (174 mg, 4.35 mmol), followed by flash column chromatographic purification on silica gel (Wakogel® C-300, 40 ml, elution with hexane-ethyl acetate 1 1) to give the title compound (2.02 g, 88.1% yield)

Workup

  1. customobtained in Reference Example 3-1)

Sources & evidence

ORD record
ord-16fcf5d97c30422d9b944aed4390c592
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

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