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

Base Information

• Chemical Name: methyl (2S,3R,4R)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)prolinate
• CAS No.: 269730-15-6
• Molecular Formula: C₂₇H₂₉N₃O₈
• Molecular Weight: 523.543
• Mol file: 269730-15-6.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about methyl (2S,3R,4R)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dioxo-1,3-dihydro-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:

phthalimide (136918-14-4,85-41-6) → methyl (2S,3R,4R)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)prolinate (269730-15-6)

Guidance literature:

Multi-step reaction with 5 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

With dmap; disodium hydrogenphosphate; dipotassium peroxodisulfate; water; sodium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile; 1: Mitsunobu reaction / 2: Reduction / 3: Acylation / 4: Hydrolysis / 5: Esterification;

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 (2S,3R,4R)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)prolinate (269730-15-6)

Guidance literature:

Multi-step reaction with 5 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

With dmap; disodium hydrogenphosphate; dipotassium peroxodisulfate; water; sodium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile; 1: Mitsunobu reaction / 2: Reduction / 3: Acylation / 4: Hydrolysis / 5: Esterification;

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

Reference yield:

benzyl (1S,4R,5R)-4-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate → methyl (2S,3R,4R)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)prolinate (269730-15-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2: H₂O; Na₂CO₃ / tetrahydrofuran

3: ethyl acetate; diethyl ether

With dmap; water; sodium carbonate; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; 1: Acylation / 2: Hydrolysis / 3: Esterification;

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

upstream raw materials:

diazomethane

(2S,3R,4R)-3-tert-Butoxycarbonylamino-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

phthalimide

Downstream raw materials:

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