Triethylamine → HCID 131711644, compound

HRID 1659570Notes

Reaction equation

C(N(CC)CC)C.Cl.[Cl:9][C:10]([Cl:27])([Cl:26])[CH2:11][O:12][C:13]([C:15]1[N:20]2[C:21](=[O:24])[CH:22]([NH2:23])[C@H:19]2[S:18][CH2:17][C:16]=1[CH3:25])=[O:14].Cl[C:29]1[C:34]([O:35][C:36](=[O:53])[CH:37]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:38](OC2C=CC=CC=2)=[O:39])=[C:33](Cl)[C:32](Cl)=[C:31](Cl)[C:30]=1Cl>C(Cl)Cl>[Cl:27][C:10]([Cl:9])([Cl:26])[CH2:11][O:12][C:13]([C:15]1[N:20]2[C:21](=[O:24])[CH:22]([NH:23][C:38](=[O:39])[CH:37]([C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)[C:36]([O:35][C:34]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:53])[C@H:19]2[S:18][CH2:17][C:16]=1[CH3:25])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

2.8 ml. (0.02 moles) of triethylamine are added to a suspension of 3.8 g. (0.01 mole) of 7-amino-3-methyl-ceph-3-em-4-carboxylic acid trichloroethyl ester hydrochloride in 30 ml. of methylene chloride. The separated triethylamine hydrochloride is filtered off, the filtrate is cooled to 0° C., and 5.02 g (0.01 mole) of phenylmalonic acid phenylester pentachlorophenyl ester are added. The obtained clear solution is stirred at the same temperature for 30 minutes, thereafter it is washed with 2 n aqueous hydrochloride acid and the solvent is evaporated. The residue is treated with absolute ethanol. 4.7 g. (80%) of 7-(α-phenoxycarbonyl-phenylacetamido)-3-methyl-ceph-3-em-4-carboxylic acid trichloroethyl ester are obtained. The white, crystalline substance melts at 120°-125° C.

Workup

filtrationThe separated triethylamine hydrochloride is filtered off
washit is washed with 2 n aqueous hydrochloride acid
customthe solvent is evaporated
additionThe residue is treated with absolute ethanol

Sources & evidence

ORD record: ord-4b54c246e6e4433bb6f4a9ea6b2ab16b
Source dataset: uspto-grants-1981_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04304717

Reaction notes

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