1,5-Diazabicyclo(5,4,0)undec-5-ene → HCID 20526317, compound

HRID 27739Notes

Reaction equation

HRID 27739 reaction equation
[CH2:1]([CH:8]1[C:14](=[O:15])[N:13]2[CH:9]1[CH2:10][C:11](Cl)([S:26]([CH2:28][CH3:29])=[O:27])[CH:12]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N12CCCCC1C=NCCC2>C(OCC)(=O)C>[CH2:1]([CH:8]1[C:14](=[O:15])[N:13]2[CH:9]1[CH2:10][C:11]([S:26]([CH2:28][CH3:29])=[O:27])=[C:12]2[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 20526338Benzyl 6-benzyl-3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 20526317HCID 20526317, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 6-benzyl-3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (79) (0.020 g) in ethyl acetate (2 ml) was treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (0.0069 g). It was stirred for 15 mins. at room temperature and then the solution was washed with brine and dried over sodium sulphate. Concentration of the solution gave benzyl 6-benzyl-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (80) (0.016 g) as a colourless gum; νmax (CHCl3) 2990, 1790, 1725 and 1590 cm-1 ; λmax (ethanol) 308 nm; τ (CDCl3) 2.5-2.9 (10H, m, phenyls), 4.66 and 4.82 (2H, ABq J 12 Hz, OCH2), 5.99 (1H, ddd J 10, 8 and 3 Hz, C5-H), 6.39 (1H, ddd J 9 6 and 3 Hz, C6-H), 6.6-7.2 (4H, m, C4-H2 and C8-H2), 7.20 (2H, q J 71/2 Hz, SCH2) and 8.76 (3H, t J 71/2 Hz, CH3); (M+ at m/e 409.1333 C23H23NO4S requires 409.1348).

Workup

  1. washat room temperature and then the solution was washed with brine
  2. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-72d97ca9793249689e1d2c905c3c1c87
Source dataset
uspto-grants-1980_09
Patent number
US04223038

Reaction notes

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