By Morris, Rene Goscinny
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Chem. , 65, H. Klesper, F. Steinfatt, I. 8995 89951. E. Sianesi, R. Redaelli, Ann. Chirn. Chim. (Rorne, (Rome, Italy) 1967,57, 1967, 57, 1426. 1426. H. Beecken, Chern. Chem. Ber. 1967,100,2151. 1967, 100, 2151. H. Beecken, Chern. Chem. Ber. 1967,100,2164. 1967, 100, 2164. J. Heterocycl. Chern. Chem. 1967,4,403. 1967, 4, 403. B. M. Snader, 1. J. Org. Org. Chern. Chem. 1967,32, 1967, 32, 506. A. Macaluso, J. Hamer,. 1. B. Loev, US 3303190,1967; 3303190, 1967; Chern. Chem. , 66, 65486. 1967; Chern.
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1. NH2CH2CO2Me 2 CH 2C0 2 Me La(OTfh, La(OTf)3, K2CO toluene, reflux reflux CHO K 2C0 3, 3 , toluene, cliO 2. 2. NaBH NaBH4, MeOH 4 , MeOH CH CH2CI 0 ~C 2 CI 22,, O°C 3. NaOH NaOH (aq) (aq) 3. ~HCHO, dimethyifumarate fumarate ~HO, dimethyl Ph Ph CO2Me toluene, reflux reflux toluene, "CO2Me Ph" ~ Ph 53 Scheme 16. 16. Synthesis Synthesisof of diad diad 53. 53. Scheme Porphyrins in Diels-Alder and 1,3-dipolar cycloaddition reactions 57 A convenient route to N-(porphyrin-2-ylmethyl)glycine 52 was described by Cavaleiro and coworkers <06JOC8352> <06JOC8352> (Scheme 16); 16); it involves the coupling of of the Ni(II) complex of of beta-formyl-meso-tetraphenylporphyrin beta-formyl-meso-tetraphenylporphyrin with an excess of of glycine methyl ester hydrochloride followed by reduction of the product imine with sodium borohydride and alkaline hydrolysis.
A Lucky Luke Adventure 2: Ghost Town by Morris, Rene Goscinny