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

HRID 1189400Notes

Reaction equation

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

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-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-yl]-acetylamino}-propionic acid methyl ester (470 mg, 1.43 mmol) in dry THF (5 mL) was added at 0° C. to solution of (methoxycarbonylsulfamoyl)triethylammonium hydroxide (455 mg, 1.83 mmol) in dry THF (10 mL) and the resulting suspension was stirred at 0° C. for 20 min, followed by 15 min at rt. 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 (1:1→1:0 EA-Hept) gave the title compound as a yellow oil. TLC: rf (EA)=0.6. LC-MS-conditions 02: tR=0.70 min, [M+H2O+H]+=329.90.

Workup

waitfollowed by 15 min at rt
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 (1:1→1:0 EA-Hept)

Sources & evidence

ORD record: ord-ffabfc8f01444c649826f9754ba213e9
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08674111B2

Reaction notes

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