Water → Diethyl 2-((isopropyl)amino)thiophene-3,4-dicarboxylate

HRID 131574Notes

Reaction equation

[CH2:1]([O:3][C:4]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[CH:26]([N:29]=[C:30]=[S:31])([CH3:28])[CH3:27].Br[CH2:33][C:34](=O)[C:35]([O:37][CH2:38][CH3:39])=[O:36].O>C1COCC1>[CH:26]([NH:29][C:30]1[S:31][CH:33]=[C:34]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:6]=1[C:4]([O:3][CH2:1][CH3:2])=[O:5])([CH3:28])[CH3:27]

Participants

Conditions

Temperature: -78 °C

Procedure

Ethoxycarbonylmethylene triphenyl phosphorane (33.8 g) in dry THF (200 ml) was treated with isopropyl isothiocyanate (10.1 g) at 65° C. for 16 h under nitrogen. The mixture was cooled to −78° C. and ethyl bromo-pyruvate (19.5 g) was added. The reaction was allowed to warm slowly to room temperature. After 24 h at room temperature more ethyl bromo-pyruvate (3.17 g) was added and the mixture was stirred at room temperature for 16 h. The reaction was poured into water (1.5 L) and extracted into ether. Drying and evaporation gave an oil which was chromatographed (SiO2/5:1 isohexane-ethyl acetate) to afford the subtitle compound (21.2 g). δ 1HCDCl3 1.23-1.43 (12H, m), 3.46 (1H, m), 4.2-4.35 (4H, m), 6.50 (1H, s), 7.52 (1H, br.d)

Workup

temperatureto warm slowly to room temperature
extractionextracted into ether
customDrying
customevaporation
customgave an oil which
customwas chromatographed (SiO2/5:1 isohexane-ethyl acetate)

Sources & evidence

ORD record: ord-76c525657b4847d8834fd30940cac0cc
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07384950B2

Reaction notes

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