Triethylamine → HCID 131711640, compound

HRID 426816Notes

Reaction equation

[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:8][C:9]1([CH3:21])[S:13][C@@H:12]2[C@H:14]([NH2:17])[C:15](=[O:16])[N:11]2[C@H:10]1[C:18]([OH:20])=[O:19].Cl[C:23]1[C:28]([O:29][C:30](=[O:47])[CH:31]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:32](OC2C=CC=CC=2)=[O:33])=[C:27](Cl)[C:26](Cl)=[C:25](Cl)[C:24]=1Cl>C(Cl)Cl>[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[O:29]([C:30]([CH:31]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:32]([NH:17][CH:14]1[C:15](=[O:16])[N:11]2[CH:10]([C:18]([O-:20])=[O:19])[C:9]([CH3:21])([CH3:8])[S:13][C@H:12]12)=[O:33])=[O:47])[C:28]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

11.2 ml. (0.08 moles) or triethylamine are added to a suspension of 8.63 g (0.04 moles) of 6-APA in 120 ml. of methylene chloride. The obtained solution is cooled to 0° C. and 21 g. (0.04 moles) of phenylmalonic acid phenylester pentachlorophenylester are added in small portions so that the temperature of the mixture does not rise above +5° C. The mixture is stirred at 0° to +5° C. for one hour, thereafter the solvent is evaporated in vacuo, and the residue is triturated with 150 ml. of ethyl acetate. The separated crystalline substance is filtered off, and washed with ethyl acetate. 20 g. (90%) of 6-(α-phenoxycarbonyl-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid triethylammonium salt are obtained. M.p.: 125°-130° C.

Workup

customdoes not rise above +5° C
customthe solvent is evaporated in vacuo
customthe residue is triturated with 150 ml
filtrationThe separated crystalline substance is filtered off
washwashed with ethyl acetate

Sources & evidence

ORD record: ord-6d89e71019424f8eb8a910709af96512
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04171303

Reaction notes

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