Nitrogen → HCID 67365195, compound

HRID 42873Notes

Reaction equation

N#N.[Cl:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[CH2:6][O:7][C:8](=[O:24])[NH:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C:16]2[N:17]=[C:18]([CH:21](O)[OH:22])[O:19][CH:20]=2)[N:11]=1.[CH3:29][Mg]Br.[NH4+].[Cl-]>C1COCC1>[Cl:3][C:4]1[CH:28]=[CH:27][CH:26]=[CH:25][C:5]=1[CH2:6][O:7][C:8](=[O:24])[NH:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C:16]2[N:17]=[C:18]([CH:21]([OH:22])[CH3:29])[O:19][CH:20]=2)[N:11]=1

Participants

Conditions

Temperature: -65 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(2-dihydroxymethyl-oxazol-4-ylmethyl)-2H-[1,2,3]triazol-4-yl]-carbamic acid 2-chloro-benzyl ester (19 mg, 0.05 mmol) in THF (1.0 mL) was treated at −65° C. with methylmagnesium bromide (0.15 mL of a 1M solution in THF, 0.15 mmol). The reaction mixture was then stirred at −65° C. for 1 h. The reaction mixture was then slowly warmed to rt and stirred at this temperature for 45 min. Sat. aq. NH4Cl was then added and the aq. layer was extracted with EA (3×10 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. The residue was purified by FC (EA) to give the title compound as a yellow oil. TLC: rf (EA)=0.30. LC-MS-conditions 02: tR=0.89 min, [M+H]+=378.30.

Workup

temperatureThe reaction mixture was then slowly warmed to rt
stirringstirred at this temperature for 45 min
extractionthe aq. layer was extracted with EA (3×10 mL)
dry with materialextracts were dried over Na2SO4
filtrationfiltered
customthe solvents were removed under reduced pressure
customThe residue was purified by FC (EA)

Sources & evidence

ORD record: ord-6fed5a318e824a0abf35ecd30694f39d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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