methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

Base Information

• Chemical Name: methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate
• CAS No.: 215719-42-9
• Molecular Formula: C₁₈H₂₅N₃O₅
• Molecular Weight: 363.414
• Mol file: 215719-42-9.mol

Synonyms:methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

Chemical Property of methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate

There total 13 articles about methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}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: 96.0%

methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-37-2) → methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-42-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In N,N-dimethyl-formamide;

DOI:10.1039/a804412k

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)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-42-9)

Guidance literature:

Multi-step reaction with 8 steps

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

2: methylhydrazine / dimethylformamide / 1.5 h / 80 °C

3: 5.0 g / Et₃N / CH₂Cl₂

4: 77 percent / K₂S₂O₈; Na₂HPO₄*2H₂O / H₂O; acetonitrile / 0.92 h / Heating

5: 60 percent / Et₃N; DMAP / CH₂Cl₂ / 1 h

6: H₂O; Na₂CO₃ / tetrahydrofuran

7: 1.26 g / ethyl acetate; diethyl ether

8: 96 percent / H₂ / Pd/C / dimethylformamide / 36 h

With dmap; disodium hydrogenphosphate; dipotassium peroxodisulfate; water; hydrogen; sodium carbonate; triethylamine; triphenylphosphine; methylhydrazine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Mitsunobu reaction / 2: hydrazinolysis / 3: Acylation / 4: Reduction / 5: Acylation / 6: Hydrolysis / 7: Esterification / 8: Catalytic hydrogenation;

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

Reference yield:

(2S,3R,4R)-4-Benzoylamino-3-tert-butoxycarbonylamino-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester → methyl (2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate (215719-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.26 g / ethyl acetate; diethyl ether

2: 96 percent / H₂ / Pd/C / dimethylformamide / 36 h

With hydrogen; palladium on activated charcoal; In diethyl ether; ethyl acetate; N,N-dimethyl-formamide; 1: Esterification / 2: Catalytic hydrogenation;

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

upstream raw materials:

methyl (2S,3R,4R)-4-(benzoylamino)-1-[(benzyloxy)carbonyl]-3-{[(tert-butoxy)carbonyl]amino}prolinate

(1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

(1S,4R,5R)-4-Benzoylamino-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2,6-dicarboxylic acid 2-benzyl ester 6-tert-butyl ester

(1S,4R,5R)-4-Benzoylamino-6-(2,4-dimethoxy-benzyl)-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester

Downstream raw materials:

((3S,7R,8R,8aS)-8-Amino-7-benzoylamino-1,4-dioxo-octahydro-pyrrolo[1,2-a]pyrazin-3-yl)-acetic acid

tert-butyl (3S,7R,8R,8aS)-7-(benzoylamino)-8-{[(tert-butoxy)carbonyl]amino}octahydro-1,4-dioxopyrrolo[1,2-a]pyrazine-3-acetate

methyl {N²-[(benzyloxy)carbonyl]-O⁴-(tert-butyl)-L-aspart-1-yl}-(2S,3R,4R)-4-(benzoylamino)-3-{[(tert-butoxy)carbonyl]amino}prolinate