Potassium → HCID 11142198, compound

HRID 1609160Notes

Reaction equation

C(O[C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:11])(=O)C.[K].[CH3:21][O:22][CH2:23][C:24]([OH:26])=[S:25]>O1CCOCC1.C(OCC)(=O)C.O.[Br-].[Zn+2].[Br-]>[CH3:21][O:22][CH2:23][C:24]([S:25][C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15])[CH3:11])=[O:26]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 4-(R)acetoxy-3(R)-[1(R)t-butyldimethylsilyloxyethyl]azetidin-2-one (2.87 g) in dioxane (40 ml) the potassium salt of methoxythioacetic acid (1.7 g) was added. Zinc bromide (2.7 g) was added to the resulting suspension and the reaction mixture was stirred for 4 hours at 40° C. The reaction mixture was then cooled at room temperature and poured in a mixture of ethyl acetate and water. The organic layer was separated, washed twice with water, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography to give 2.99 g of the title product (90% yield). NMR (CDCl3) δ (ppm): 0.1 (6H, s); 0.83 (9H, s); 1.16 (3H, d); 3.13 (1H, dd); 3.42 (3H, s), 4.01 (2H, s) 4.20 (1H, m); 5.22 (1H, d); 6.55 (1H, s)

Workup

temperatureThe reaction mixture was then cooled at room temperature
customThe organic layer was separated
washwashed twice with water
dry with materialdried over anhydrous sodium sulfate
customevaporated in vacuo
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-08cc6159facc4027a3f51f98fd6f97c6
Source dataset: uspto-grants-1995_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05399679

Reaction notes

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