Nitrogen → [2-(2-Hydroxymethyl-oxazol-4-ylmethyl)-2H-[1,2,3]triazol-4-yl]-carbamic acid 2-chloro-benzyl ester

HRID 42871Notes

Reaction equation

N#N.[Cl:3][C:4]1[CH:34]=[CH:33][CH:32]=[CH:31][C:5]=1[CH2:6][O:7][C:8](=[O:30])[NH:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C:16]2[N:17]=[C:18]([C:21](C)(C)[O:22][SiH2]C(C)(C)C)[O:19][CH:20]=2)[N:11]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>C1COCC1>[Cl:3][C:4]1[CH:34]=[CH:33][CH:32]=[CH:31][C:5]=1[CH2:6][O:7][C:8](=[O:30])[NH:9][C:10]1[CH:14]=[N:13][N:12]([CH2:15][C:16]2[N:17]=[C:18]([CH2:21][OH:22])[O:19][CH:20]=2)[N:11]=1

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 {2-[2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-ylmethyl]-2H-[1,2,3]triazol-4-yl}-carbamic acid 2-chloro-benzyl ester (144 mg, 0.30 mmol) in dry THF (3.0 mL) was treated at 0° C. with TBAF (0.46 mL of a 1M solution in THF, 0.46 mmol). The reaction mixture was stirred at 0° C. for 30 min. Sat. aq. NH4Cl (5 mL) was added, the layers separated and the aq. layer extracted with EA (3×10 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure. Purification of the residue by FC (EA) gave the title compound as a yellow oil. TLC: rf (EA)=0.25. LC-MS-conditions 01: tR=0.82 min; [M+H]+=363.90.

Workup

customthe layers separated
extractionthe aq. layer extracted with EA (3×10 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification of the residue by FC (EA)

Sources & evidence

ORD record: ord-ee10f0077d6544afa0d035c25fb5638a
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536209B2

Reaction notes

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