1,5-Diazabicyclo(5,4,0)undec-5-ene → HCID 20526310, compound

HRID 67932Notes

Reaction equation

HRID 67932 reaction equation
Cl[C:2]1([S:20]([CH2:22][CH3:23])=[O:21])[CH2:8][CH:7]2[N:4]([C:5](=[O:9])[CH2:6]2)[CH:3]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].N12CCCCC1C=NCCC2>C(OC(=O)C)C>[CH2:22]([S:20]([C:2]1[CH2:8][CH:7]2[N:4]([C:5](=[O:9])[CH2:6]2)[C:3]=1[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11])=[O:21])[CH3:23]

Participants

4

Reactant 2

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 20526303Benzyl 3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 20526310HCID 20526310, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of benzyl 3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (54) (0.020 g) in ethylacetate (2 ml) was stirred at room temperature under argon and treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (0.009 g). After a period of 15 minutes the reaction mixture was washed with brine and dried over sodium sulphate. It was concentrated to give a single diastereoisomer of benzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (55) (0.017 g) as a gum; νmax (CHCl3) 2980, 1795 and 1730 cm-1 ; τ(d6 -acetone) 2.5-2.8 (5H, m, phenyl), 4.78 (2H, s, benzyl CH2), 5.71 (1H, tdd J9,5 and 3 Hz, C5-H), 6.49 (1H, dd J17 and 5 Hz, C6-H), 6.82 (2H, d J 9 Hz, C4-H2), 6.84 (1H, dd J17 and 3 Hz, C6-H), 7.13 and 7.15 (2H, 2q J71/2 Hz, SCH2) and 8.80 (3H, t J71/2 Hz, CH3).

Workup

  1. washAfter a period of 15 minutes the reaction mixture was washed with brine
  2. dry with materialdried over sodium sulphate
  3. concentrationIt was concentrated

Sources & evidence

ORD record
ord-43418384cc6e4f718a02772fbdeded79
Source dataset
uspto-grants-1982_08
Patent number
US04347181

Reaction notes

Loading…