Pyridine → HCID 70507776, compound
Reaction equation
N1C=CC=CC=1.[CH3:7][C:8]1[CH2:17][S:16][C@@H:11]2[C@H:12]([NH2:15])[C:13](=[O:14])[N:10]2[C:9]=1[C:18]([OH:20])=[O:19].C(#N)C.[CH2:24]([O:31][C:32](=[O:54])[CH:33]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:34](OC1C(Cl)=C(Cl)C(Cl)=C(Cl)C=1Cl)=[O:35])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([O:31][C:32]([CH:33]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:34]([NH:15][CH:12]1[C:13](=[O:14])[N:10]2[C:9]([C:18]([OH:20])=[O:19])=[C:8]([CH3:7])[CH2:17][S:16][C@H:11]12)=[O:35])=[O:54])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
1.8 ml. of pyridine are added to a suspension of 2.17 g. (0.01 mole) of 7-ADCA in 40 ml. of acetonitrile and 2 ml. of water. The obtained solution is cooled to 0° C., 5.6 g. (0.01 mole) of phenylmalonic acid pentachlorophenylester benzylester are added, and the mixture is stirred for 4 hours. The acetonitrile is evaporated, the residue is taken up in 50 ml. of ethyl acetate, and the ethyl acetate solution is admixed with saturated sodium bi-carbonate solution. The aqueous phase is washed with ethyl acetate, thereafter it is covered with 50 ml. of ethyl acetate, and acidified to pH=2 with 2 n aqueous hydrochloric acid. The ethyl acetate phase is separated, dried, and evaporated. 3.5 g. (75%) of 7-(α-benzyloxycarbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid are obtained with a purity degree of 95% (determined by titrimetry).
Workup
- customThe acetonitrile is evaporated
- washThe aqueous phase is washed with ethyl acetate
- customThe ethyl acetate phase is separated
- customdried
- customevaporated
Sources & evidence
- ORD record
- ord-a8e8688bbe5a4ea2b0c59d8b8d4625fe
- Source dataset
- uspto-grants-1979_10
- Patent number
- US04171303
Reaction notes
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