Water → 7beta-Phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester

HRID 2420538Notes

Reaction equation

HRID 2420538 reaction equation
[N+:1]([C:4]1[CH:48]=[CH:47][C:7]([CH2:8][O:9][C:10](=[O:46])/[C:11](/[N:19]2[CH:22]([S:23]S(C3C=CC(C)=CC=3)(=O)=O)[CH:21]([NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[C:20]2=[O:45])=[C:12](\N2CCCC2)/[CH3:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(C)C=CC=CC=1.C(OCC)(=[O:58])C.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C(#N)C.C1C=CC=CC=1>[N+:1]([C:4]1[CH:48]=[CH:47][C:7]([CH2:8][O:9][C:10]([C:11]2[N:19]3[C:20](=[O:45])[C@@H:21]([NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C@H:22]3[S:23][CH2:13][C:12]=2[OH:58])=[O:46])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 12784133HCID 12784133, compoundHCID 21584019Toluene ethylacetate

Product 1

HCID 547167947beta-Phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 160 mg (0.23 mmol) of a mixture consisting of 2-[4-(p-toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-(1-pyrrolidyl)-crotonic acid p-nitrobenzyl ester and the corresponding isocrotonic acid ester in 3 ml of dry acetonitrile is heated under nitrogen for about 4 hours at 80° C until no further starting material can be detected by thin layer chromatography (silica gel; toluene/ethyl acetate, 1:1). The heating bath is removed, p-toluenesulphonic acid (about 0.23 mmol) and 0.2 ml of water are added to the reaction mixture containing the 7β-phenoxyacetamido-3-pyrrolidino-cephem-4-carboxylic acid p-nitrobenzyl ester and the mixture is stirred for a further 2 hours at room temperature. The reaction mixture is diluted with benzene, washed with water, dried over sodium sulphate and evaporated in vacuo. The residue is triturated at 0° C with diethyl ether and gives the pale yellow 7β-phenoxyacetamido-3-hydroxy-3-cephem-4-carboxylic acid p-nitrobenzyl ester. IR spectrum (methylene chloride): characteristic bands at 2.95; 3.3; 5.6; 5.75 (sh); 5.9; 5.95 (sh); 6.55; 7.45; 8.15 and 8.3μ; NMR spectrum (deuterochloroform): δ in ppm: 3.4 (2H, 2, J = 17 Hz); 4.57 (2H, s); 5.06 (1H, d; J=5 Hz); 5.35 (2H, q, J = 14 Hz); 5.7 (1H, dd, J = 5.10 Hz); 6.8-8.4 (10H, c) and 11.4 (1H, br.s.).

Workup

  1. customThe heating bath is removed
  2. washwashed with water
  3. dry with materialdried over sodium sulphate
  4. customevaporated in vacuo
  5. customThe residue is triturated at 0° C with diethyl ether

Sources & evidence

ORD record
ord-91c862ef79764cfb8670356457ed1b66
Source dataset
uspto-grants-1978_08
Patent number
US04110533

Reaction notes

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