Tetrahydrofuran → HCID 14460289, compound

HRID 1031042Notes

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>[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 1 N solution of lithium bis-trimethylsilylamide in tetrahydrofuran (THF) are added dropwise with stirring at -70° C. to a solution of 1.91 g (12 mmol) of tert-butylthioazetidin-2-one in 6 ml of dry N,N-dimethylformamide (DMF) and then a solution of 4.93 g (18 mmol) of p-nitrobenzyl bromoacetate in 6 ml of DMF is added dropwise to the mixture and the mixture is stirred at -30° C. for a further 30 minutes. Dilution of the reaction mixture with 100 ml of toluene, washing with three portions of 50 ml each of water, drying the organic phase over magnesium sulphate and evaporating the solvent in vacuo yields 4.3 g of solid crude product, which is chromatographed on 120 g of silica gel using toluene/ethyl acetate (4:1). The purified product (2.6 g) is recrystallized from 100 ml of dry isopropanol.

Workup

washDilution of the reaction mixture with 100 ml of toluene, washing with three portions of 50 ml each of water
dry with materialdrying the organic phase over magnesium sulphate
customevaporating the solvent in vacuo

Sources & evidence

ORD record: ord-39555710e1bc46829693a0f4ad1f1377
Source dataset: uspto-grants-1992_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05108747

Reaction notes

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