Tetrahydrofuran → p-Nitrobenzyl (4-tert-butylthio-2-oxo-1-azetidinyl)acetate

HRID 2371892Notes

Reaction equation

C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].[C:11]([S:15]N1CCC1=O)([CH3:14])([CH3:13])[CH3:12].Br[CH2:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24].[O:36]1C[CH2:39][CH2:38][CH2:37]1>CN(C)C=O.C1(C)C=CC=CC=1>[C:11]([S:15][CH:39]1[N:5]([CH2:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)=[O:24])[C:37](=[O:36])[CH2:38]1)([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -30 °C

Procedure

14.4 ml of a 1N solution of lithium bistrimethylsilylamide in tetrahydrofuran (THF) are added dropwise to a stirred solution of 1.91 g (12 mmol) of tert-butylthioazetidin-2-one in 6 ml of dry N,N-dimethylformamide (DMF) at -70° C., and a solution of 4.93 g (18 mmol) of p-nitrobenzyl bromoacetate in 6 ml of DMF is subsequently added dropwise to the mixture, and the mixture is then stirred for a further 30 minutes at -30° C. The reaction mixture is diluted with 100 ml of toluene and washed with three 50 ml portions of water, the organic phase is dried over magnesium sulphate, and the solvent is evaporated in vacuo to give 4.3 g of a solid crude product, which is chromatographed over 120 g silica gel using toluene:ethyl acetate (4:1). The purified product (2.6 g) is recrystallized from 100 ml of dry isopropanol. Yield 2.09 g of melting point 82.5°-84° C. IR spectrum in methylene chloride: 2955, 1770, 1755, 1610, 1530, 1390, 1375, 1365, 1345, 1180, 1110, 945, 915, 855, 845 cm-1.

Workup

washwashed with three 50 ml portions of water
dry with materialthe organic phase is dried over magnesium sulphate
customthe solvent is evaporated in vacuo

Sources & evidence

ORD record: ord-c4823de5812949748b880edb56bb44d5
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05096899

Reaction notes

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