Reaction SMILES: [C:1]1([CH:7]([O:14][C:15]([CH:17]2[N:22]3[C:23](=[O:34])[CH:24]([C:25](=[O:33])[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C@H:21]3[S:20][C:19]([NH2:35])=[C:18]2[CH2:36][C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([O:44][CH3:45])[CH:38]=2)=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>N1C=CC=CC=1.C(N(CC)CC)C>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:34])[C@@H:24]([C:25](=[O:33])[CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C@H:21]3[S:20][CH:19]([NH2:35])[C:18]=2[CH2:36][C:37]2[CH:42]=[CH:41][C:40]([OH:43])=[C:39]([O:44][CH3:45])[CH:38]=2)=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
Reactant: COc1cc(CC2=C(N)S[C@@H]3C(C(=O)Cc4ccccc4)C(=O)N3C2C(=O)OC(c2ccccc2)c2ccccc2)ccc1O
Solvent: CCN(CC)CC
Solvent: c1ccncc1
Product: COc1cc(CC2=C(C(=O)OC(c3ccccc3)c3ccccc3)N3C(=O)[C@@H](C(=O)Cc4ccccc4)[C@H]3SC2N)ccc1O

Procedure:
A solution of 6.1 g of 3-(4-hydroxy-3-methoxybenzyl)-7-phenylacetyl-amino-ceph-2-em-4ξ-carboxylic acid diphenylmethyl ester in 63.5 ml of absolute pyridine and 6.5 ml of triethylamine is left to stand for 31/2 days under nitrogen at room temperature, then evaporated to dryness several times while adding toluene. The residue is separated by chromatography on 330 g of silica gel; elution is carried out with methylene chloride containing 3% methyl acetate, fractions of 250 ml each being taken. The 3-(4-hydroxy-3-methoxy-benzyl)-7β-phenylacetyl-amino-ceph-3-em-4-carboxylic acid diphenylmethyl ester is isolated in fractions 6-8, whereas fractions 9 and 10 contain a mixture of the product and the starting material. The succeeding fractions 11-16 contain principally unchaged starting material. The material from fractions 9 and 10 and the mother liquors of the crystallised products (from a mixture of methylene chloride, diethyl ether and cyclohexane) of fractions 6-8 are chromatographed once more on 130 g of silica gel. Elution is effected with methylene chloride containing 1% of ethyl acetate, fractions of 100 ml each being taken. 3-(4-Hydroxy-3-methoxy-benzyl)-7β-phenylacetyl-amino-ceph-3-em-4-carboxylic acid diphenylmethyl ester, which is almost pure according to chromatography, is eluted in fractions 6-18. These fractions are crystallised from a mixture of methylene chloride, diethyl ether and cyclohexane; the 3-(4-hydroxy-3-methoxybenzyl)-7β-phenylacetyl-amino-ceph-3-em-4-carboxylic acid diphenylmethyl ester melts at 166°-167° (the analytical sample is dried for 15 hours under a high vacuum at 35° and still contains cyclohexane according to the nuclear reasonance spectrum). The solvent can be completely removed after final drying for 20 hours at 45°; m.p. 166°-167.5°C (uncorr.) [α]D20 = -92° ± 1° (c = 0.968 in chloroform): thin-layer chromatogram (silica gel): Rf = 0.70 (system: toluene/ethyl acetate 1:1), Rf = 0.50 (system: toluene/ethyl acetate 2:1), Rf = 0.44 (system: toluene/acetone 4:1) and Rf = 0.21 (system: toluene/acetone 9:1) (the Rf values of the corresponding ceph-2-em compound are 0.68, 0.46, 0.40 and 0.15, respectively); ultraviolet absorption spectrum (in 95% ethanol): λmax = 272 mμ (ε = 9150) and λmin = 244 mμ (ε = 7300); infrared absorption spectrum: characteristic bands at: 2,78μ, 3,02μ, 5,60μ, 5,83μ, 6,02μ, 6,54μ, 6,60μ, 7,90μ, 8,08μ, 8,56μ, 8,90μ, 9,12μ and 14,41μ (in mineral oil) and 2,80μ, 2,90μ, 5,60μ, 5,78μ, 6,21μ, 6,61μ, 7,27μ, 8,12μ, 8,28μ, 8,50μ and 8,62μ (in methylene chloride).