Pyridine → 4(S)-(imidazole-1-carbothioyloxy)-tetrahydro-thiopyran-3(R)-carboxylic acid methyl ester

HRID 2214049Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[C@@H:10]([OH:11])[CH2:9][CH2:8][S:7][CH2:6]1)=[O:4].[C:12](N1C=CN=C1)([N:14]1[CH:18]=[CH:17][N:16]=[CH:15]1)=[S:13].N1C=CC=CC=1>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C@H:5]1[C@@H:10]([O:11][C:12]([N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[S:13])[CH2:9][CH2:8][S:7][CH2:6]1)=[O:4]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4(S)-hydroxy-tetrahydro-thiopyran-3(R)-carboxylic acid methyl ester (1.00 g, 5.674 mmol) in dry tetrahydrofuran (50 mL), under argon, was treated with 1,1′-thiocarbonyldiimidazole (2.085 g, 11.35 mmol) and pyridine (6.88 μL, 8.511 mmol). The reaction mixture was stirred at 25° C. for 36 h and was then diluted with ethyl acetate (100 mL). The resulting solution was washed sequentially with a saturated aqueous sodium bicarbonate solution (1×50 mL) and a saturated aqueous sodium chloride solution (1×50 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40M, Silica, 4/1 hexanes/ethyl acetate) afforded 4(S)-(imidazole-1-carbothioyloxy)-tetrahydro-thiopyran-3(R)-carboxylic acid methyl ester (901 mg, 55.4%) as a beige oil: EI-HRMS m/e calcd for C11H14N2O3S2 (M+) 286.0446, found 286.0438.

Workup

washThe resulting solution was washed sequentially with a saturated aqueous sodium bicarbonate solution (1×50 mL)
dry with materialThe combined organic extracts were dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5588058885474039ae6f4b949f93a82a
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105671B2

Reaction notes

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