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

HRID 2371824Notes

Reaction equation

HRID 2371824 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]([NH:62][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]([NH:62][CH3:63])=[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 10679921Phosphonic acid, 2-(methylamino)-2-oxoethyl-, diethyl ester

Product 1

HCID 67792453(E)-3-[(2S,4S)-N-allyloxycarbonyl-4-tritylthiopyrrolidin-2-yl]-N-methylacrylamideYield 89.7%

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 the Reference Example 3-1); 4.60 g, 10.0 mmol), dimethyl sulfoxide (1.99 ml, 28.0 mmol), oxalyl chloride (1.28 ml, 15.0 mmol), triethylamine (6.98 ml, 50.0 mmol), 2-(diethylphosphono)-N-methylacetamide (2.32 g, 11.0 mmol) and 60% sodium hydride (420 mg, 10.5 mmol), followed by flash column chromatographic purification on silica gel (Wakogel® C-300, 100 ml, elution with hexaneethyl acetate 1:2) to give the title compound (4.60 g, 89.7% yield).

Workup

  1. customobtained in the Reference Example 3-1)

Sources & evidence

ORD record
ord-058215dfd7704d208623d1f7c29d7d49
Source dataset
uspto-grants-1992_03
Patent number
US05095013

Reaction notes

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