Triethylamine → HCID 131711636, compound

HRID 1659563Notes

Reaction equation

HRID 1659563 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].[CH2:22]1[C:30]2[C:25](=[CH:26][C:27]([O:31][C:32](=[O:54])[CH:33]([C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[C:34](OC3C(Cl)=C(Cl)C(Cl)=C(Cl)C=3Cl)=[O:35])=[CH:28][CH:29]=2)[CH2:24][CH2:23]1>ClCCl>[CH2:1]([NH+:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH2:22]1[C:30]2[C:25](=[CH:26][C:27]([O:31][C:32]([CH:33]([C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:34]([NH:17][CH:14]3[C:15](=[O:16])[N:11]4[CH:10]([C:18]([O-:20])=[O:19])[C:9]([CH3:21])([CH3:8])[S:13][C@H:12]34)=[O:35])=[O:54])=[CH:28][CH:29]=2)[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 110826-Aminopenicillanic acidHCID 53988050HCID 53988050, compound

Product 1

HCID 131711636HCID 131711636, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

12.88 ml. (0.092 moles) of triethylamine are added to a suspension of 9.66 g (0.046 moles) of 6-APA in 150 ml. of dichloromethane, and the mixture is stirred at room temperature until a solution is obtained. The solution is cooled to 0° C., and 25 g. (0.046 moles) of phenyl-malonic acid pentachlorophenylester 5-indanylester are added to it at such a rate that the temperature of the mixture always remains below "5° C. The mixture is stirred at 0° C. for one hour, and thereafter the solvent is evaporated in vacuo. The residue is admixed with 100 ml. of ethyl acetate, whereupon 26 g. (98%) of 6-(α-[5-indanyloxy-carbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid triethylammonium salt separate in the form of a crystalline substance. M.p.: 153°-155° C.

Workup

  1. customis obtained
  2. customalways remains below "5° C
  3. customthe solvent is evaporated in vacuo
  4. custom(98%) of 6-(α-[5-indanyloxy-carbonyl]-phenylacetamido)-2,2-dimethyl-penam-3-carboxylic acid triethylammonium salt separate in the form of a crystalline substance

Sources & evidence

ORD record
ord-a487622f543c4fbe835fdc6f87fcfa86
Source dataset
uspto-grants-1981_12
Patent number
US04304717

Reaction notes

Loading…