(S)-2-((R)-2-Carboxymethyl-1-oxo-2,5-diaza-spiro[3.4]octane-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-((R)-2-Carboxymethyl-1-oxo-2,5-diaza-spiro[3.4]octane-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 914389-47-2
• Molecular Formula: C₁₈H₂₇N₃O₆
• Molecular Weight: 381.429
• Mol file: 914389-47-2.mol

Synonyms:

Chemical Property of (S)-2-((R)-2-Carboxymethyl-1-oxo-2,5-diaza-spiro[3.4]octane-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((R)-2-Carboxymethyl-1-oxo-2,5-diaza-spiro[3.4]octane-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 8 articles about (S)-2-((R)-2-Carboxymethyl-1-oxo-2,5-diaza-spiro[3.4]octane-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 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:

(4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one (914389-46-1) → (S)-2-((R)-2-Carboxymethyl-1-oxo-2,5-diaza-spiro[3.4]octane-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (914389-47-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; under 760 Torr;

DOI:10.1021/jo061189l

Reference yield:

(+/-)-2-(4-methoxyphenyl)-2,5-diazaspiro[3,4]octan-1-one (914389-37-0,914389-38-1) → (S)-2-((R)-2-Carboxymethyl-1-oxo-2,5-diaza-spiro[3.4]octane-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (914389-47-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: L-Boc-Phe-OH / ethyl acetate; hexane

1.2: aq. NaHCO₃ / CH₂Cl₂ / 0.17 h

2.1: 50 percent / HOBt; DCC / tetrahydrofuran / 48 h / 20 °C

3.1: 65 percent / aq. CAN / acetonitrile / 0 °C

4.1: 52 percent / Cs₂CO₃ / acetonitrile / 4 h / 20 °C

5.1: H₂ / Pd/C / ethyl acetate; methanol / 760 Torr

With ammonium cerium(IV) nitrate; N-tert-butoxycarbonyl-L-phenylalanine; hydrogen; benzotriazol-1-ol; caesium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate; acetonitrile;

DOI:10.1021/jo061189l

Reference yield:

2-oxomethylene-pyrrolidine-1-carboxylic acid benzyl ester → (S)-2-((R)-2-Carboxymethyl-1-oxo-2,5-diaza-spiro[3.4]octane-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (914389-47-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 12 h / -40 - 20 °C

2.1: 98 percent / H₂ / Pd/C / ethyl acetate; methanol / 760 Torr

3.1: L-Boc-Phe-OH / ethyl acetate; hexane

3.2: aq. NaHCO₃ / CH₂Cl₂ / 0.17 h

4.1: 50 percent / HOBt; DCC / tetrahydrofuran / 48 h / 20 °C

5.1: 65 percent / aq. CAN / acetonitrile / 0 °C

6.1: 52 percent / Cs₂CO₃ / acetonitrile / 4 h / 20 °C

7.1: H₂ / Pd/C / ethyl acetate; methanol / 760 Torr

With ammonium cerium(IV) nitrate; N-tert-butoxycarbonyl-L-phenylalanine; boron trifluoride diethyl etherate; hydrogen; benzotriazol-1-ol; caesium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1021/jo061189l

upstream raw materials:

(4R)-2-[(benzyloxycarbonyl)methyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one

(+/-)-2-(4-methoxyphenyl)-2,5-diazaspiro[3,4]octan-1-one

(4R)-2-(4-methoxyphenyl)-2,5-diazaspiro[3,4]octan-1-one

(+/-)-5-benzyloxycarbonyl-2-(4-methoxyphenyl)-2,5-diazaspiro[3,4]octan-1-one

Downstream raw materials:

(4R)-2-[3-aza-4-(benzyloxycarbonyl)-2-oxobutyl]-5-[(2S)-1-tert-butoxycarbonylpyrrolidin-2-ylcarbonyl]-2,5-diazaspiro[3,4]octan-1-one