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ChemicalBook CAS DataBase List 3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester synthesis

2synthesis methods
6066-82-6 Synthesis
N-Hydroxysuccinimide

6066-82-6
729 suppliers
$5.00/10g

23761-23-1 Synthesis
3-Oxocyclobutanecarboxylic acid

23761-23-1
450 suppliers
$6.00/1g

3-Oxo-cyclobutanecarboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

939412-81-4
15 suppliers
inquiry

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Yield:-

Reaction Conditions:

with dicyclohexyl-carbodiimide in ethyl acetate at 16 - 45; for 2 h;

Steps:


Into a 5L reactor equipped with a nitrogen flow and an overhead stirrer was added N-hydroxysuccinimide (250.0 g, 2.172 mol) and 3-oxo-cyclobutanecarboxylic acid (248 g, 2.17 mol). Ethyl acetate (3.4 L) was added and the reaction was cooled to 16° C. A solution of 25% DCC in EtOAc (2.17 mol) was added slowly via an addition funnel to the reaction mixture over 7 minutes then the mixture was then heated at 45° C. After 2 h, the mixture was filtered and the filtrate was washed once with EtOAc (1L×1) and evaporated to dryness in vacuo to afford the desired product. 1H NMR (400 MHz, DMSO-d6) δ 2.83 (bs, 4H), 3.30-3.39 (m, 2H), 3.52-3.60 (m, 2H) and 3.67-3.73 (m, 1H).

References:

Chen, Xin;Coate, Heather;Crew, Andrew Philip;Dong, Han-Qing;Honda, Ayako;Mulvihill, Mark Joseph;Tavares, Paula A.R.;Wang, Jing;Werner, Douglas S.;Mulvihill, Kristen Michelle;Siu, Kam W.;Panicker, Bijoy;Bharadwaj, Apoorba;Arnold, Lee D.;Jin, Meizhong;Volk, Brian;Weng, Qinghua;Beard, James David US2007/112005, 2007, A1 Location in patent:Page/Page column 61