Nitrogen → HCID 67128497, compound

HRID 1189410Notes

Reaction equation

N#N.[CH3:3][O:4][C:5](=[O:25])[CH:6]([NH:9][C:10](=[O:24])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2([CH3:23])[O:22][CH2:21][CH2:20][O:19]2)[CH:13]=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:24][C:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]3([CH3:23])[O:22][CH2:21][CH2:20][O:19]3)[CH:13]=2)=[N:9]1)=[O:25]

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-{2-[3-(2-methyl-[1,3]dioxolan-2-yl)-phenyl]-acetylamino}-propionic acid methyl ester (2.30 g, 7.11 mmol) in dry THF (28.5 mL) was added at 0° C. to solution of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (2.09 g, 8.50 mmol) in dry THF (28.5 mL) and the resulting suspension was stirred at 0° C. for 25 min. The reaction mixture was then stirred at reflux for 1 h. The mixture was then allowed to cool down to rt and filtered. The filter cake was rinsed with ether and EA and the filtrate was concentrated under reduced pressure. Purification of the residue by FC (7:3 EA-Hept) gave the title compound as a yellow oil. TLC: rf (7:3 EA-Hept)=0.34.

Workup

stirringThe reaction mixture was then stirred
temperatureat reflux for 1 h
temperatureto cool down to rt
filtrationfiltered
washThe filter cake was rinsed with ether and EA
concentrationthe filtrate was concentrated under reduced pressure
customPurification of the residue by FC (7:3 EA-Hept)

Sources & evidence

ORD record: ord-7c48a45df12d4b8fb54f2d770caea19a
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674111B2

Reaction notes

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