Formaldehyde → (R)-tert-butyl 4-((ethyldisulfanyl)methyl)-5-oxooxazolidine-3-carboxylate
Reaction equation
[CH3:1]C1(C)[C@@H]2CC[C@@]1(CS(O)(=O)=O)C(=O)C2.C=O.[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:30][S:31][S:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(NC2CCCCC2)CCCCC1>C1(C)C=CC=CC=1>[CH2:33]([S:32][S:31][CH2:30][C@H:26]1[C:27](=[O:29])[O:28][CH2:1][N:25]1[C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH3:34]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
((1S,4R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid (1.07 g, 4.62 mmol) and paraformaldehyde (847 mg, 2.89 mmol) were added to a solution of dicyclohexylamine (R)-2-((tert-butoxycarbonyl)amino)-3-(ethyldisulfanyl)propanoate (Compound 2d-f) (2.00 g, 4.32 mmol) in toluene (8 ml), and the mixture was stirred at 100° C. overnight. The reaction solution was then returned to room temperature and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→87/13) to afford (R)-tert-butyl 4-((ethyldisulfanyl)methyl)-5-oxooxazolidine-3-carboxylate (2e-F) (847 mg, 67%).
Workup
- customwas then returned to room temperature
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→87/13)
Sources & evidence
- ORD record
- ord-c81c2d8ceb0747cc89aeaa8fc8234d17
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409952B2
Reaction notes
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