Water → 2-Methyl-2-{[4-(2-phthalimidoethyl)-1,3-thiazol-2-yl]thio}propionic acid tert-butyl ester

HRID 914286Notes

Reaction equation

[C:1]([O:5][C:6](=[O:23])[C:7]([CH3:22])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16]OS(C)(=O)=O)[N:14]=1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[C:24]1(=[O:34])[NH:28][C:27](=[O:29])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12.[K].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:23])[C:7]([CH3:8])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][N:28]2[C:27](=[O:29])[C:26]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]3[C:24]2=[O:34])[N:14]=1)[CH3:22])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 85 °C

Procedure

2-Methyl-2-[(4-{2-[(methylsulfonyl)oxy]ethyl}-1,3-thiazol-2-yl)thio]propionic acid tert-butyl ester (123 g) synthesized in Example 5 was dissolved in N,N-dimethylformamide (800 mL), potassium phthalimide (59.7 g) was added thereto and the mixture was stirred for 2 hr at 85° C. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1) to give the title compound (136 g) as a slightly yellow oil.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record: ord-36248a033ac34f8f8f89840ed745fc8f
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026370B2

Reaction notes

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