Final-140C-Fall2005

Final-140C-Fall2005 - Student Name: Problem 1 Starting from...

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Unformatted text preview: Student Name: Problem 1 Starting from Boc-LyS—OtBu, provide a strategy for the synthesis of Glutamic acid. ( Show the chemical structures of all intermediates and provide all the reagents needed for all steps to perform the synthesis. (25 points) 0- OH Boc-Lys-O’Bu OH NH; H2N O .)TFA fbcvt. H a» '3 I”, Q A) 03’ X0 /“"“a r, \’< X0 luv xo\£ W“? jl O \\” g: 2.) “‘04, O 0 H15; Student Name: Problem 2 Phenylglycine is a non natural amino acid. Using Strecker synthesis and appropriate reagents and techniques, provide a synthetic approach for the synthesis of L—phenylglycine starting from nitrobenzene. (20 points) No2 ???‘? OH _—_>. H2N O 5%911‘42‘3 ‘ / _fflfiD&a M59 .4. Saparhflv‘it-i‘: ' “Mflw‘mfirw' at; aways»; =mgwflwmuvmuusmm 5w ‘KI up / 227 ‘9 ' I ’0“ 9 O I “N 5 o .4. / O 3 w ‘) HOMO @mwwmwmwmg 0.4 + “ “fir-Q “at; “to no (if) H gbnAm'V Ht“ 5" t J ”“w"‘u’° ' w J . i]; i ' 6 nub,ch 4/ _ , Q) .Cu‘a ) 9 04cm | C / \H L: GEN / 9 L‘. «on H Q0 L y to L) H+/H30 Q *9 A) 80th flJprom / ‘ ““QH M k“ / M, E J.) an“... GM! 4 Student Name: Problem 3 (25 points) Starting from polystyrene methyl chloride resin: Using the appropriate protected amino acids, reagents and techniques, provide a Cl synthetic approach for the solid-phase synthesis of the following product: bigger: H 0 me you 0 “ESL,” / 0H HP or ng Mob! 4 Km; m 9m. N“ o Student Name: Problem 4 Draw the chemical structure of the major products expected from each of the following reactions. A) (12 points) Excess HF Pro-Lys-Val —————> A g ____.)... B + B) (12 points) DCC in DCM Boc~.N/l\n,oH + thxfo\tBu ; D + E + F H O O ‘ 9 PD -: gecmu’i‘fl/uu H’Jlxox I - O x "x Student Name: Problem 5 Give the major product of each of the followifig reactions. (30 points) “(A a) [& HNO3 0&3“ <3 >~TMO£ O m)“ Mme!“ MN.- \N/ I n’ j b) I \ \N neg N/ ' ' “is \ . / 1 c) I / CsH5L| \ N c: —"’ "i 1)MgIEt20 #- / \\ 25w / \ 2) 602 u / / l. d) QBr , (k: ‘1!) H Cl 3) H30+ ” \ Kg 3 e) 1)(Ph)aP .- ‘ ‘ O=O “\g' , —--—> < / ——* I" * ‘ 2) BuLi m- _ “03 H 1)0H'IHO —-—>— \M ' ———>-2 M n O 2) CH3-S-CH3 I ‘ ‘ H _ - o 2)0H,Heat - MHN/ Cl 1)A|C| g) [:I/W ~—>3 fl/kl o 2) EtNHz |§ /\/ 3) NaBH3CN not 0 o , h) YNoz + §)J\ M Wkam} H+‘ Student Name: Problem 6 a) For the following reaction, give the structures of compounds A, B, C and D. Show the stereochemistry. (16 points) 0 o—/< 0 Q4 on 1) Dcc, >= HOBt in DCM 1) “2"” L-Cysteine—h- A B ___,.._ c -—p._ D reflux Et3N in DMF 2) O/\NH2 O O 2) )LOJK S >< \: 5 Pyridine, DMF A ‘ I'm/\Il’ou B“: 111’” M a 'a-J\° 0 Q egg: 5mm “\fiwz W \CM J J H \Aflzg’ “:9 ,0 ”\ Student Name: Problem 7 Complete the following reactions: (36 points) .9 o B 9 "O Nu 3) AJLOH 4—;- 914 ——-—————)-> Trace P ’4! 8r - Q U 0 0 ‘ -j..m 0 scolz l NH Brz, NaOH 4 H20 u N H Na+N3- M7N 5 1)LiAlH4, A0“ \IN L ) -—)n- ——-——>— c I Lea. 2) H+IH20 Ch 0 1) H+ d) NH H ———> N _ 2) NaBHacN V :4 a C; 3 ' I . o )‘s M Q“ “LL e) + + HCI, EtOH, he a. N +- . <:>=o Hac—~’(l_I HM > —4 k x] N0 4 H N f) N NaNOz, HCI, Hi0 ( 1 L7 W A? o u a“ 3 + U “a I 2) CH3I \ / Student Name; Problem 8 a) Using curved arrows, provide a detailed reaction mechanism and all reagents and intermediates needed for the following reactions. Name the final product. (10 points) + '3’ s o _"_"' ©‘% \gt/w W Li... _€_&l€5\- 2r . s 657 s 8 Want? ‘ 4127*» xxl‘ \‘Ca WWW“ we or N: (5 “ if” [iv-.94 “M4, it "What b) Name the following compounds. (16 points) No2 I Q 3— Mttm -Ben-2=<sm med (9 ’ OH Mo“ 3 - Ewomo - Lt “mawthfifiJmfiaic aw cocaine. in LAN/CU . 75 a Bro mm was} wmal‘ngl hemn C9 Milo N” “5H° Aimaigji hemmmxmtééj 10 .4 ...
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This note was uploaded on 04/07/2008 for the course CHEM 140C taught by Professor Nefzi during the Spring '06 term at UCSD.

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Final-140C-Fall2005 - Student Name: Problem 1 Starting from...

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