Ethyl Acetate → HCID 13854074, compound

HRID 256053Notes

Reaction equation

[O:1]=[C:2]1[CH:8]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH2:7][S:6][CH:5]([C:20]2[CH:24]=[CH:23][S:22][CH:21]=2)[CH2:4][NH:3]1.Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].[H-].[Na+].C(OCC)(=O)C>CN(C)C=O.O>[O:1]=[C:2]1[CH:8]([N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])[CH2:7][S:6][CH:5]([C:20]2[CH:24]=[CH:23][S:22][CH:21]=2)[CH2:4][N:3]1[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 4.1 g of 5-oxo-6-phthalimido-2-(3-thienyl)perhydro-1,4-thiazepine [prepared as described in step (e) above] in 60 ml of dimethylformamide were added dropwise 2.2 g of t-butyl bromoacetate, followed by 593 mg of a 55% w/w suspension of sodium hydride in oil at 0° to -5° C. under a stream of nitrogen. The reaction mixture was stirred at 0° C. for 20 minutes and then poured into a mixture of ethyl acetate and water. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate, and the solvent was evaporated off. The semi-solid residue was collected by filtration using ethyl acetate and diisopropyl ether, to yield 3.7 g of the title compound, melting at 157°-160° C. (with decomposition).

Workup

customThe ethyl acetate layer was separated
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
customthe solvent was evaporated off
filtrationThe semi-solid residue was collected by filtration

Sources & evidence

ORD record: ord-04adb6c8ccbf42afb57a098274d68027
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04699905

Reaction notes

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