1,5-Diazabicyclo(5,4,0)undec-5-ene → Benzyl 3-(2-acetamidoethylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 67933Notes

Reaction equation

HRID 67933 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7]([C:9]1(Cl)[CH2:15][CH:14]2[N:11]([C:12](=[O:16])[CH2:13]2)[CH:10]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:8])(=[O:3])[CH3:2].N12CCCCC1C=NCCC2>C(OCC)(=O)C>[C:1]([NH:4][CH2:5][CH2:6][S:7]([C:9]1[CH2:15][CH:14]2[N:11]([C:12](=[O:16])[CH2:13]2)[C:10]=1[C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 20526351HCID 20526351, compound

Product 1

HCID 20526356Benzyl 3-(2-acetamidoethylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 76.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of benzyl 3-(2-acetamidoethylsulphinyl)-3-chloro-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (62) (0.010 g) in ethyl acetate (1 ml) was treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (0.0037 g) under an argon atmosphere. It was stirred at room temperature for 15 minutes and then washed with brine and dried over sodium sulphate. The solution was concentrated to give benzyl 3-(2-acetamidoethylsulphinyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (63) (0.007 g) as a colourless gum; νmax (CHCl3) 3400, 2980, 2920, 1795, 1920, 1670, 1600 and 1515 cm-1 ; νmax (ethanol) 305 nm; τ(CDCl3) 2.5-2.8 (5H, m, phenyl), 4.76 (2H, s, benzyl CH2), 5.6-5.9 (1H, m, C5-H), 6.3-7.3 (8H, m, C4-H2, C6-H2, NCH 2 CH2S) and 8.14 (3H, s, COCH3).

Workup

  1. washwashed with brine
  2. dry with materialdried over sodium sulphate
  3. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-cb2699af0cfe40fd84feeb54304f8f6b
Source dataset
uspto-grants-1982_08
Patent number
US04347181

Reaction notes

Loading…