Methyl N-(triethylammoniosulfonyl)carbamate → Methyl {2-{4-[(1H-Benzimidazol-1-yl)methyl]phenyl}-5-methyl-1,3-oxazol-4-yl}carboxylate

HRID 1716830Notes

Reaction equation

[N:1]1([CH2:10][C:11]2[CH:27]=[CH:26][C:14]([C:15]([NH:17][C@H:18]([C:22]([O:24][CH3:25])=[O:23])[C@@H:19]([CH3:21])O)=[O:16])=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[N:1]1([CH2:10][C:11]2[CH:27]=[CH:26][C:14]([C:15]3[O:16][C:19]([CH3:21])=[C:18]([C:22]([O:24][CH3:25])=[O:23])[N:17]=3)=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

Conditions

Temperature: 60 °C

Procedure

A stirred solution of methyl N-[4-(1H-benzimidazol-1-ylmethyl)benzoyl]thre-oninate (0.34 g, 0.94 mmol) in THF was treated with Burgess reagent (0.27 g, 1.12 mmol), heated to 60° C., stirred for 2 h at 60° C., cooled to room temperature and concentrated under reduced pressure. The resultant residue was purified by column chromatography (silica, CH2Cl2:CH3OH 95:5) to afford the title product in 47% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 350 (MH+).

Workup

temperaturecooled to room temperature
concentrationconcentrated under reduced pressure
customThe resultant residue was purified by column chromatography (silica, CH2Cl2:CH3OH 95:5)

Sources & evidence

ORD record: ord-678c031ab5a04f319a64a63a99a7f6d8
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803825B2

Reaction notes

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