HCID 86648519, compound → Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-(1-hydroxypropyl)-1,3-thiazole-5-carboxylate

HRID 43511Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[C:9]1[S:10][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH:14]=[O:15])[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:28]([Mg]Br)[CH3:29]>C(OCC)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]([C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])[C:9]1[S:10][C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:12]([CH:14]([OH:15])[CH2:28][CH3:29])[N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

Ethyl 2-[bis(tert-butoxycarbonyl)amino]-4-formyl-1,3-thiazole-5-carboxylate obtained in Example (62d) (915.5 mg, 2.29 mmol) was dissolved in diethyl ether (30 mL), followed by cooling to −78° C. Then, tetrabutylammonium bromide (890 mg, 2.76 mmol) and ethylmagnesium bromide (1 M solution in THF, 2.8 mL) were added, and the mixture was stirred for one hour. Diethyl ether was added to the reaction solution, and the organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, the residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=91/9, 85/15) to obtain 327.2 mg of the title compound (33%).

Workup

washthe organic layer was washed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentration under reduced pressure
customthe residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=91/9, 85/15)

Sources & evidence

ORD record: ord-265f792dde574d2bb27b917244e6edcb
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Reaction notes

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