1-Bromo-2,2-dimethoxypropane → {2-[4-(4-Methyl-oxazol-2-yl)-phenoxy]-ethyl}-carbamic acid benzyl ester

HRID 49372Notes

Reaction equation

[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[NH2:21])=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][C:26](OC)(OC)[CH3:27]>O>[CH2:1]([O:8][C:9](=[O:23])[NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]2[O:22][CH:25]=[C:26]([CH3:27])[N:21]=2)=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

[2-(4-Carbamoyl-phenoxy)-ethyl]-carbamic acid benzyl ester (322 mg, 1.02 mmol) and 1-bromo-2,2-dimethoxypropane (3.8 g, 20.4 mmol) were combined in a round-bottomed flask and heated to about 130° C. for about thirty minutes. The reaction mixture was then cooled to room temperature and poured into water. The mixture was extracted with ethyl acetate, the combined extracts dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting crude material was purified by column chromatography (1:1 hexanes/ethyl acetate) to afford the desired oxazole product (167 mg, 47% yield). LRMS ([M+H]+)=353.1.

Workup

temperatureThe reaction mixture was then cooled to room temperature
extractionThe mixture was extracted with ethyl acetate
dry with materialthe combined extracts dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting crude material was purified by column chromatography (1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-755b4dd35d7d4dbdb6b16dbe7f4a2fe0
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06706743B2

Reaction notes

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