Ethyl Acetate → HCID 89533661, compound

HRID 1050979Notes

Reaction equation

[NH2:1][C:2]1[C:3]([OH:19])=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@@H:8]1[C:12]([O:14][CH3:15])=[O:13])=[O:6].[CH3:20][O:21][C:22]1[C:23](=O)[C:24](=[O:28])[C:25]=1[O:26]C.C(OCC)(=O)C>C(O)C>[OH:19][C:3]1[C:2]([NH:1][C:23]2[C:24](=[O:28])[C:25](=[O:26])[C:22]=2[O:21][CH3:20])=[CH:18][CH:17]=[CH:16][C:4]=1[C:5]([N:7]1[CH2:11][CH2:10][CH2:9][C@@H:8]1[C:12]([O:14][CH3:15])=[O:13])=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 2.64 g (10 mmol, 1 eq) of methyl (R)-1-(3-amino-2-hydroxybenzoyl)pyrrolidine-2-carboxylate and 2.84 g (20 mmol, 2.0 eq) of 3,4-dimethoxy-3-cyclobutene-1,2-dione in 80 ml of ethanol was heated at 50° C. for four and a half hours. The residue was taken up with ethyl acetate and washed three times with a 1 M aqueous sodium dihydrogen phosphate solution. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated. The oil was chromatographed on silica gel (300 g prepacked column) eluted with heptane/ethyl acetate (gradient). 1.27 g of methyl (R)-1-[2-hydroxy-3-(2-methoxy-3,4-dioxocyclobut-1-enylamino)benzoyl]pyrrolidine-2-carboxylate were obtained in the form of white solid. Yield=34%.

Workup

washwashed three times with a 1 M aqueous sodium dihydrogen phosphate solution
dry with materialThe organic phase was dried over anhydrous sodium sulfate
filtrationfiltered
customevaporated
customThe oil was chromatographed on silica gel (300 g prepacked column)
washeluted with heptane/ethyl acetate (gradient)

Sources & evidence

ORD record: ord-f9aab0ffa65b444789ac8173d5e35cb4
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388149B2

Reaction notes

Loading…