methyl N²-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate

Base Information

• Chemical Name: methyl N²-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate
• CAS No.: 269730-21-4
• Molecular Formula: C₃₅H₄₂N₄O₁₁
• Molecular Weight: 694.739

Synonyms:methyl N²-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate

Chemical Property of methyl N²-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate

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Technology Process of methyl N²-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate

There total 8 articles about methyl N²-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

Z-D(tBu)-OH (5545-52-8) + methyl (2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate (269730-20-3) → methyl N2-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate (269730-21-4)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R

Reference yield:

phthalimide (136918-14-4,85-41-6) → methyl N2-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate (269730-21-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 61 percent / PPh₃; DEAD / tetrahydrofuran / 19 h / -30 - 20 °C

2: 82 percent / K₂S₂O₈; Na₂HPO₄*2H₂O / H₂O; acetonitrile / 0.5 h / Heating

3: 74 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h

4: H₂O; Na₂CO₃ / tetrahydrofuran

5: ethyl acetate; diethyl ether

6: 100 percent / H₂ / Pd/C / dimethylformamide / 72 h

7: 63 percent / HATU; 1-hydroxy-7-aza-1H-benzotriazole; i-Pr₂EtN / CH₂Cl₂ / 24 h / 20 °C

With dmap; disodium hydrogenphosphate; dipotassium peroxodisulfate; 1-hydroxy-7-aza-benzotriazole; water; hydrogen; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Mitsunobu reaction / 2: Reduction / 3: Acylation / 4: Hydrolysis / 5: Esterification / 6: Catalytic hydrogenation / 7: Acylation;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R

Reference yield:

(1S,4S,5S)-6-(2,4-Dimethoxy-benzyl)-4-hydroxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester → methyl N2-{[(benzyloxy)carbonyl]-L-aspart-1-yl}-(2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate (269730-21-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 61 percent / PPh₃; DEAD / tetrahydrofuran / 19 h / -30 - 20 °C

2: 82 percent / K₂S₂O₈; Na₂HPO₄*2H₂O / H₂O; acetonitrile / 0.5 h / Heating

3: 74 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h

4: H₂O; Na₂CO₃ / tetrahydrofuran

5: ethyl acetate; diethyl ether

6: 100 percent / H₂ / Pd/C / dimethylformamide / 72 h

7: 63 percent / HATU; 1-hydroxy-7-aza-1H-benzotriazole; i-Pr₂EtN / CH₂Cl₂ / 24 h / 20 °C

With dmap; disodium hydrogenphosphate; dipotassium peroxodisulfate; 1-hydroxy-7-aza-benzotriazole; water; hydrogen; sodium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Mitsunobu reaction / 2: Reduction / 3: Acylation / 4: Hydrolysis / 5: Esterification / 6: Catalytic hydrogenation / 7: Acylation;

DOI:10.1002/(SICI)1522-2675(20000216)83:2<444::AID-HLCA444>3.0.CO;2-R

upstream raw materials:

Z-D(tBu)-OH

methyl (2S,3R,4R)-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)prolinate

phthalimide

methyl (2S,3R,4R)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)prolinate

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