Sodium hydride → Diethyl 1-(2-(tert-butoxycarbonylamino)ethyl)-3-methoxy-1H-pyrrole-2,4-dicarboxylate

HRID 1019828Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][NH:5][C:4]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+].[C:20]([O:24][C:25]([N:27]1[CH2:31][CH2:30]OS1(=O)=O)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[C:20]([O:24][C:25]([NH:27][CH2:31][CH2:30][N:5]1[CH:6]=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:2][CH3:1])=[C:4]1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:26])([CH3:23])([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of diethyl 3-methoxy-1H-pyrrole-2,4-dicarboxylate (93 mmol) in DMF (340 ml) was added 60% NaH (140 mmol) in portions at 0° C. and the reaction mixture was stirred at 25° C. for 0.5 h. 2,2-Dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (93 mmol) was added at 0° C. and the mixture was allowed to warm to 25° C. and stirred for 21 h. The reaction was quenched with ethanol at 0° C. The solvent was evaporated under vacuum. Yield: 35 g (98% yield)

Workup

temperatureto warm to 25° C.
stirringstirred for 21 h
customThe reaction was quenched with ethanol at 0° C
customThe solvent was evaporated under vacuum

Sources & evidence

ORD record: ord-4523ef333b2d474d99e87775e991b0f4
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716293B2

Reaction notes

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