Ethylene → HCID 10837843, compound

HRID 1901456Notes

Reaction equation

HRID 1901456 reaction equation
C=C.[C:3]1([CH2:9][C:10]([NH:12][C@@H:13]2[C:40](=[O:41])[N:15]3[C:16]([C:28]([O:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=4)=[O:29])=[C:17](OS(C(F)(F)F)(=O)=O)[CH2:18][S:19][C@H:14]23)=[O:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:42](N(C(C)C)CC)(C)[CH3:43]>C(OCC)(=O)C>[O:41]=[C:40]1[N:15]2[C@H:14]([S:19][C@@H:18]3[C:17](=[C:16]2[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)=[O:29])[CH2:43][CH2:42]3)[C@@H:13]1[NH:12][C:10](=[O:11])[CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6325EthyleneHCID 81531DiisopropylethylamineHCID 10769651HCID 10769651, compound

Product 1

HCID 10837843HCID 10837843, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Ethylene was bubbled into a solution of p-methoxybenzyl (6R,7R)-7-phenylacetamido-3-(trifluoromethanesulphonyloxy)ceph-3-em-4-carboxylate (0.50 g, 0.852 mmol) in ethyl acetate (500 ml) whilst a solution of diisopropylethylamine (0.15 ml, 0.852 mmol) in ethyl acetate (100 ml) was added dropwise over 2 h. After completion of the addition the mixture was left to stand for 18 h then the solvent was evaporated under reduced pressure. The residue was chromatographed to give the title compound (0.24 g, 61%), (Found: M+, 464.1411. C25H24N2O5S requires M, 464.1406); νmax (CH2Cl2) 1786, 1722, 1686, 1604 cm-1 ; δH (CDCl3) 2.08 (1H, m), 2.46 (1H, dtd, J 10.4, 9.3, 3.2), 3.16 (1H, dtd, J 15.8, 9.4, 1.6), 3.28 (1H, ddt, J 15.8, 8.8, 3.0). 3.63 (2H, ABq, J 16.1), 3.80 (3H, s), 4.32 (1H, dddd, J 9.3, 8.2, 2.8, 1.5), 4.94 (1H, d, J 5.0), 5.18 (2H, ABq, J 11.9), 5.76 (1H, d, J 8.8, 5.0), 5.97 (1H, d, J 8.8), 6.87 (2H, d, J 8.7), 7.26 (7H, m).

Workup

  1. additionwas added dropwise over 2 h
  2. additionAfter completion of the addition the mixture
  3. waitwas left
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-1fde626f8aab4accb9ff82f5e63c64e9
Source dataset
uspto-grants-1996_11
Patent number
US05578592

Reaction notes

Loading…