Triethylamine → HCID 131711638, compound

HRID 426815Notes

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].ClC1C([O:29][C:30](=O)[CH:31]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:32]([O:34][C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([CH3:42])[CH:36]=2)=[O:33])=C(Cl)C(Cl)=C(Cl)C=1Cl>ClCCl>[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:42][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][C:38]=1[CH3:41])[O:34][C:32]([CH:31]([C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)[C:30]([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:29])=[O:33]

Participants

Conditions

Temperature: 0 °C

Procedure

3.6 ml. (0.026 moles) of triethylamine are added to a suspension of 2.8 g. (0.013 moles) of 6-APA in 50 ml. of dichloromethane, and the mixture is stirred at room temperature until a clear solution is obtained. The solution is cooled to 0° C., 7 g. (0.013 moles) of phenylmalonic acid 3,4-dimethylphenylester pentachlorophenylester are added, and the mixture is stirred at the same temperature for one hour. Thereafter the solvent is evaporated in vacuo, and the residue is admixed with 30 ml. of ethyl acetate. 7.5 g (95%) of 6-(α-[3,4-dimethylphenoxycarbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid triethylammonium salt separate in the form of a white, crystalline substance. M.p.: 155°-160° C.

Workup

customis obtained
customThereafter the solvent is evaporated in vacuo
custom7.5 g (95%) of 6-(α-[3,4-dimethylphenoxycarbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid triethylammonium salt separate in the form of a white, crystalline substance

Sources & evidence

ORD record: ord-5793d76f4dda4c81999e6930a3b6ff63
Source dataset: uspto-grants-1979_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04171303

Reaction notes

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