Nitrogen → 2-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

HRID 1189359Notes

Reaction equation

N#N.[CH3:3][O:4][C:5](=[O:22])[CH:6]([NH:9][C:10](=[O:21])[CH2:11][CH2:12][CH2:13][CH2:14][C:15]1([CH3:20])[O:19][CH2:18][CH2:17][O:16]1)[CH2:7]O.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1>[CH3:3][O:4][C:5]([CH:6]1[CH2:7][O:21][C:10]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2([CH3:20])[O:19][CH2:18][CH2:17][O:16]2)=[N:9]1)=[O:22]

Participants

Conditions

Temperature: 0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 3-hydroxy-2-[5-(2-methyl-[1,3]dioxolan-2-yl)-pentanoylamino]-propionic acid methyl ester (1.40 g, 4.84 mmol) in dry THF (15 mL) was added at −10° C. to a solution of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (1.43 g, 5.81 mmol) in dry THF (35 mL) and the resulting suspension was stirred at 0° C. for 1.5 h. The reaction mixture was then stirred at reflux overnight. The mixture was then allowed to cool down to rt and filtered. The filtrate was concentrated under reduced pressure to give the title compound as a pale yellow oil. TLC: rf (1000:50:4 CH2Cl2-MeOH—NH3)=0.45.

Workup

stirringThe reaction mixture was then stirred
temperatureat reflux overnight
temperatureto cool down to rt
filtrationfiltered
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-fe103197ad134f2789f04e06282a9339
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674111B2

Reaction notes

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