1,4-Cyclohexadiene → HCID 131717662, compound

HRID 1681066Notes

Reaction equation

HRID 1681066 reaction equation
C1(C[O:8]C(=O)[NH:10][CH2:11][CH2:12][CH2:13][N:14]([CH2:24][CH2:25][P:26]([O:31][CH2:32][CH3:33])([O:28][CH2:29][CH3:30])=[O:27])[C:15]2[C:18](=[O:19])[C:17](=[O:20])[C:16]=2OCC)C=CC=CC=1.C1CC=CCC=1>[Pd].C(O)C>[OH2:8].[CH2:29]([O:28][P:26]([CH2:25][CH2:24][N:14]1[CH2:13][CH2:12][CH2:11][NH:10][C:16]2[C:17](=[O:20])[C:18](=[O:19])[C:15]1=2)(=[O:27])[O:31][CH2:32][CH3:33])[CH3:30].[O:20]=[C:17]1[C:18](=[O:19])[C:15]2[N:14]([CH2:24][CH2:25][P:26](=[O:27])([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])[CH2:13][CH2:12][CH2:11][NH:10][C:16]1=2

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 10553302HCID 10553302, compound

Product 1

HCID 131717662HCID 131717662, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a flask containing 10% palladium on carbon (2.11 g) under nitrogen was added [3-[[2-(diethoxyphosphinyl)ethyl](2-ethoxy-3,4-dioxo-1-cyclobuten-1-yl)-amino]propyl]carbamic acid phenylmethyl ester (2.11 g, 4.2 mmol) in absolute ethanol (180 mL), followed by 1,4-cyclohexadiene (4.3 mL, 45 mmol). After stirring for 5 hours, the reaction mixture was filtered through Celite® and concentrated in vacuo to yield a crude solid, which was recrystallized from methanol and ethyl acetate (total volume=20 mL), filtered, and washed with hexane to afford [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]phosphonic acid diethyl ester hemihydrate as a cream colored solid (0.82 g, 62%, mp 148°-149° C.); IR (KBr, cm-1): 1810; 1H NMR (CDCl3, 400 MHz): δ 7.50 (br s, NH), 4.18-4.10 (m, 4H), 4.09-4.00 (m, 2H), 3.51-3.46 (m, 4H), 2.19 (d of t, J=18 and 7.5 Hz, 2H), 2.10-2.04 (m, 2H), 1.34 (t, J=7 Hz, (6H).

Workup

  1. filtrationthe reaction mixture was filtered through Celite®
  2. concentrationconcentrated in vacuo
  3. customto yield a crude solid, which
  4. customwas recrystallized from methanol and ethyl acetate (total volume=20 mL)
  5. filtrationfiltered
  6. washwashed with hexane

Sources & evidence

ORD record
ord-4c56f88ecff94517b5eb3cfaf19ab3f9
Source dataset
uspto-grants-1992_12
Patent number
US05168103

Reaction notes

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