Dimethylformamide → HCID 90203154, compound

HRID 927050Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][O:10][C:11]2[CH:19]=[CH:18][C:14]([CH:15]=[N:16][OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].ClN1[C:27](=[O:28])[CH2:26][CH2:25][C:24]1=O.C(N([CH2:35][CH3:36])CC)C.CN(C=[O:41])C>C1COCC1>[CH2:35]([O:41][C:27]([C:26]1[C:15]([C:14]2[CH:18]=[CH:19][C:11]([O:10][CH2:9][C:8]3[CH:20]=[CH:21][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=3)=[CH:12][CH:13]=2)=[N:16][O:17][C:25]=1[CH3:24])=[O:28])[CH3:36]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(4-methanesulfonyl-benzyloxy)-benzaldehyde oxime (4.65 g, 15.2 mmol; made using methods described in Example 2) in DMF (10 mL) was added N-chlorosuccinimide (2.60 g, 19.5 mmol) portionwise over 30 min. The mixture was then cooled to 0° C. after which it was allowed to return to rt and stirred for 1 h. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was evaporated to yield a white solid which was suspended in THF (60 mL). Ethyl 3-(1-pyrrolidino)-crotonate (3.65 g, 19.9 mmol) and triethylamine (4 mL, 28.7 mmol) in THF (20 mL) were added to the suspension. After stirring for 18 h at rt the reaction mixture was concentrated in vacuo and loaded directly onto silica gel. Chromatography (35% ethyl acetate in hexane) afforded 3-[4-(4-methanesulfonyl-benzyloxy)-phenyl]-5-methyl-isoxazole-4-carboxylic acid ethyl ester (2.39 g, 38%) as a clear oil that solidified into white disks.

Workup

customto return to rt
extractionextracted with ethyl acetate
customThe organic layer was evaporated
customto yield a white solid which
stirringAfter stirring for 18 h at rt the reaction mixture
concentrationwas concentrated in vacuo

Sources & evidence

ORD record: ord-3ee132a6c3514da9bdf3d02482c8a265
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290465B2

Reaction notes

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