Dicyclohexylcarbodiimide → 2,5-Dioxopyrrolidin-1-yl 3-oxocyclobutanecarboxylate

HRID 448988Notes

Reaction equation

HRID 448988 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[O:9]=[C:10]1[CH2:13][CH:12]([C:14](O)=[O:15])[CH2:11]1.C1CCC(N=C=NC2CCCCC2)CC1>CCOC(C)=O>[O:9]=[C:10]1[CH2:13][CH:12]([C:14]([O:1][N:2]2[C:6](=[O:7])[CH2:5][CH2:4][C:3]2=[O:8])=[O:15])[CH2:11]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 49133583-Oxocyclobutane-1-carboxylic acid

Product 1

HCID 591330492,5-Dioxopyrrolidin-1-yl 3-oxocyclobutanecarboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
16 °C

Procedure

Into a 5 L 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). EtOAc (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 (1 L×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).

Workup

  1. customInto a 5 L reactor equipped with a nitrogen flow and an overhead stirrer
  2. temperaturethe mixture was then heated at 45° C
  3. filtrationthe mixture was filtered
  4. washthe filtrate was washed once with EtOAc (1 L×1)
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-ce14f37bac1a4370b1e71ed5f5330cf8
Source dataset
uspto-grants-2013_07
Patent number
US08481733B2

Reaction notes

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