A two-step synthesis of virstatin reactions are given. Give the yield and % yield of each synthesis. Make a labeled drawing of the equivalent hydrogens for each product. Using the NMR drawings given for each structure, describe how the hydrogens are seen on the NMR by chemical shift, integration, and splitting. Make sure your NMR matches the structure of the product you are proposing. For example: “the triplet at 4ppm, integrating to 2, represents the methylene group (Ha) attached to the nitrogen, as it deshielded by the electronegative element and is split by the neighboring methylene group. If you did not make the intended product in step one of the two step synthesis, explain why it did not matter in regards to further reacting the products to form virstatin.
A two-step synthesis of virstatin reactions are given. Give the yield and % yield of each synthesis. Make a labeled drawing of the equivalent hydrogens for each product.
Using the NMR drawings given for each structure, describe how the hydrogens are seen on the NMR by chemical shift, integration, and splitting. Make sure your NMR matches the structure of the product you are proposing. For example: “the triplet at 4ppm, integrating to 2, represents the methylene group (Ha) attached to the nitrogen, as it deshielded by the electronegative element and is split by the neighboring methylene group.
If you did not make the intended product in step one of the two step synthesis, explain why it did not matter in regards to further reacting the products to form virstatin.
Data
Mass of 1,8-naphthalimide used: 0.2528g
Mass of potassium carbonate used: 0.2624g
Recovered virstatin ethyl ester: 0.2602g
Mass of virstatin ethyl ester used in step 2: 0.1066g
Mass of recovered virstatin: 0.0035g
Volume of DMF used: 1.3ml
Volume of ethyl 4-bromobutanoate used: 0.27ml
Volume of methanol used: 1.5ml
Volume of sodium hydroxide used: 0.15ml
![Step 1
K,CO3
DMF
2'
N.
.N.
Reflux 1 hour
Br.
2
3
ethyl 4-bromobutanoate
1,8-naphthalimide
virstatin ethyl ester
Step 2
3'
3'
HO,
2'
2'
IN
1. NaOH (аq)
Methanol
Heat 30 min
N.
8
2. HC1
2
3
3
5
4'-[N-(1,8-naphthalimide)]-n-butanoic acid
(virstatin)
Virstatin ethyl ester
2.
4+](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fdc99cc4f-9438-44d8-9b43-49724a6b39cf%2Ff5b54cdd-b972-40d5-91e2-bc5450bdee74%2Fe4mwap_processed.png&w=3840&q=75)
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