Water → HCID 86687707, compound

HRID 1473637Notes

Reaction equation

[S:1]1[CH:5]=[C:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[N:3]=[CH:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1.O>CN(C=O)C>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][N:6]([C:4]2[N:3]=[CH:2][S:1][CH:5]=2)[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl thiazol-4-ylcarbamate (13.0 g, 64.9 mmol) in DMF (150 mL) was added Cs2CO3 (42.3 g, 130 mmol) and 1-(chloromethyl)-4-methoxybenzene (12.1 g, 78.0 mmol, Spectrochem). The reaction mixture was stirred at 80° C. for 6 h. The reaction mixture was allowed to cool to room temperature and water (500 mL) was added. The aqueous layer was extracted with diethyl ether (2×500 mL). The combined organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to obtain the crude material which was further purified by column chromatography (silica gel 100-200 mesh and 0-20% ethyl acetate in hexanes) to obtain tert-butyl 4-methoxybenzyl(thiazol-4-yl)carbamate (15.0 g, 80%) as an off-white solid. MS (ESI, positive ion) m/z=321 (M+1)+.

Workup

temperatureto cool to room temperature
extractionThe aqueous layer was extracted with diethyl ether (2×500 mL)
dry with materialThe combined organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customto obtain the crude material which
customwas further purified by column chromatography (silica gel 100-200 mesh and 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-a8db14130af94d36b2b40c82c7ef6450
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012443B2

Reaction notes

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