Styrene → HCID 57080368, compound

HRID 1901453Notes

Reaction equation

HRID 1901453 reaction equation
[O:1]=[S@@:2]1[C@@H:7]2[C@H:8]([NH:11][C:12](=[O:20])[CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9](=[O:10])[N:6]2[C:5]([C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[O:22])=[C:4](OS(C(F)(F)F)(=O)=O)[CH2:3]1.[CH2:41]=[CH:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.C(N(C(C)C)CC)(C)C>ClCCl>[O:1]=[S@@:2]1[C@H:7]2[N:6]([C:9](=[O:10])[C@H:8]2[NH:11][C:12](=[O:20])[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:5]([C:21]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2)=[O:22])=[C:4]2[C@@H:3]1[CH:42]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[CH2:41]2

Participants

5

Reactant 3

HCID 7501StyreneHCID 81531DiisopropylethylamineHCID 10326269HCID 10326269, compound

Product 1

HCID 57080368HCID 57080368, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of p-methoxybenzyl (1S,6R,7R)-1-oxo-7-phenylacetamido-3-trifluoromethanesulphonyloxyceph-3-em-4-carboxylate (30 mg, 0.05 mmol) and styrene (300 μl, 2.62 mmol) in dichloromethane (3 ml), was added diisopropyl-ethylamine (10 μl, 0.057 mmol). After stirring at room temperature for 30 min the mixture was chromatographed to give the title compounds (14.7 mg, 53%), νmax (CH2Cl2), 1790, 1728, 1689 cm-1 ; δH (CDCl3) 7.41-7.16 (12H, m) 6.89 (2H, m) 6.67 (0.4H, d, J 9.7 Hz), 6.52 (0.6H, d, J 9.8 Hz), 5.98 (0.4H, dd, J 9.7, 4.9 Hz), 5.86 (0.6H, dd, J 9.8, 4.9 Hz), 5.28 (ABq, J 11.9 Hz), 5.23 (0.8H, ABq, J 11.8 Hz), 4.38 (1H, m), 4.31 (0.6H, m), 4.0 (1.4H, m), 3.80 (3H, s), 3.73-3.82 (4H, m).

Workup

  1. customwas chromatographed

Sources & evidence

ORD record
ord-fe3296d0183744e68cd37d447dcafeb6
Source dataset
uspto-grants-1996_11
Patent number
US05578592

Reaction notes

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