(R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Base Information

• Chemical Name: (R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• CAS No.: 914389-54-1
• Molecular Formula: C₃₄H₄₄N₄O₉
• Molecular Weight: 652.745
• Mol file: 914389-54-1.mol

Synonyms:(R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property of (R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

There total 10 articles about (R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl 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:

2-oxomethylene-pyrrolidine-1-carboxylic acid benzyl ester → (R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (914389-54-1)

Guidance literature:

Multi-step reaction with 8 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: 97 percent / NaHCO₃ / ethyl acetate; H₂O / 2 h / 20 °C

5.1: aq. CAN / acetonitrile / 0 °C

6.1: 0.652 g / DMAP / acetonitrile / 0 - 20 °C

7.1: 87 percent / aq. NaOH / tetrahydrofuran

8.1: 0.529 g / DCC; HOBt / tetrahydrofuran / 0 - 20 °C

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

DOI:10.1021/jo061189l

Reference yield:

(+/-)-5-benzyloxycarbonyl-2-(4-methoxyphenyl)-2,5-diazaspiro[3,4]octan-1-one (914389-32-5) → (R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (914389-54-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 98 percent / H₂ / Pd/C / ethyl acetate; methanol / 760 Torr

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

2.2: aq. NaHCO₃ / CH₂Cl₂ / 0.17 h

3.1: 97 percent / NaHCO₃ / ethyl acetate; H₂O / 2 h / 20 °C

4.1: aq. CAN / acetonitrile / 0 °C

5.1: 0.652 g / DMAP / acetonitrile / 0 - 20 °C

6.1: 87 percent / aq. NaOH / tetrahydrofuran

7.1: 0.529 g / DCC; HOBt / tetrahydrofuran / 0 - 20 °C

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

DOI:10.1021/jo061189l

Reference yield:

(S)-benzyloxycarbonyl-proline acid chloride (61350-60-5,61350-62-7,89705-40-8,106709-50-6) → (R)-2-({[(R)-1-Benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester (914389-54-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Et₃N / CH₂Cl₂ / 0.75 h / -40 °C

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

3.1: 98 percent / H₂ / Pd/C / ethyl acetate; methanol / 760 Torr

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

4.2: aq. NaHCO₃ / CH₂Cl₂ / 0.17 h

5.1: 97 percent / NaHCO₃ / ethyl acetate; H₂O / 2 h / 20 °C

6.1: aq. CAN / acetonitrile / 0 °C

7.1: 0.652 g / DMAP / acetonitrile / 0 - 20 °C

8.1: 87 percent / aq. NaOH / tetrahydrofuran

9.1: 0.529 g / DCC; HOBt / tetrahydrofuran / 0 - 20 °C

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

DOI:10.1021/jo061189l

upstream raw materials:

2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester

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

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

(4R)-5-benzyloxycarbonyl-2-(tert-butoxycarbonyl)-2,5-diazaspiro[3,4]octan-1-one

Downstream raw materials:

(R)-2-({[(R)-1-Benzyloxycarbonyl-2-({[(R)-1-benzyloxycarbonyl-2-(tert-butoxycarbonylamino-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Refernces