1,5-Diazabicyclo(5,4,0)undec-5-ene → Benzyl 6-(3-methoxycarbonylprop-2-ene-1-yl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 27738Notes

Reaction equation

HRID 27738 reaction equation
Cl[C:2]1([S:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:28])[CH2:8][CH:7]2[N:4]([C:5](=[O:16])[CH:6]2[CH2:9][CH:10]=[CH:11][C:12]([O:14][CH3:15])=[O:13])[CH:3]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].N12CCCCC1C=NCCC2>C(OCC)(=O)C>[CH3:15][O:14][C:12]([CH:11]=[CH:10][CH2:9][CH:6]1[C:5](=[O:16])[N:4]2[CH:7]1[CH2:8][C:2]([S:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:28])=[C:3]2[C:17]([O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:18])=[O:13]

Participants

4

Reactant 2

HCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 54378895Benzyl 3-chloro-6-(3-methoxycarbonylprop-2-en-1-yl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 54004572Benzyl 6-(3-methoxycarbonylprop-2-ene-1-yl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 93.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 3-chloro-6-(3-methoxycarbonylprop-2-en-1-yl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0] heptane-2-carboxylate (68) (0.015 g) was stirred in ethyl acetate (2 ml) at room temperature under argon and treated with 1,5-diazabicyclo[5,4,0]undec-5-ene (0.005 g). After a period of 15 mins. the reaction mixture was washed with brine and dried over sodium sulphate. Removal of the solvent gave a single diastereoisomer of benzyl 6-(3-methoxycarbonylprop-2-ene-1-yl)-7-oxo-3-phenylsulphinyl-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (69)(0.013 g) as a gum; νmax (CHCl3) 2980, 1795, 1730, 1720, 1660 and 1045 cm-1 ; τ (d6 -acetone) 2.3-2.8 (10H, m, phenyls), 3.12 (1H, dt J 16 and 6 Hz, CH2 --CH=), 4.12 (1H, dt J 16 and 1 Hz, = CH--CO), 4.68 (2H, s, benzyl CH2), 5.72 (1H, ddd J 10, 9 and 6 Hz, C5-H), 5.9-6.3 (1H, m, C6-H), 6.39 (3H, s, OCH3), 6.81 (1H, dd J 18 and 9 Hz, C4-H), 7.25 (1H, dd J 18 and 10 Hz, C4-H) and 6.9-7.4 (2H, m, CH2 --CH=).

Workup

  1. washthe reaction mixture was washed with brine
  2. dry with materialdried over sodium sulphate
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-b3323cf9b09340c2904a1a73913e1512
Source dataset
uspto-grants-1980_09
Patent number
US04223038

Reaction notes

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