1,2-Pyrrolidinedicarboxylic acid, 5-[(2Z)-2-bromo-4-methoxy-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]- 2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,5S)-

Base Information

• Chemical Name: 1,2-Pyrrolidinedicarboxylic acid, 5-[(2Z)-2-bromo-4-methoxy-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]- 2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,5S)-
• CAS No.: 478239-48-4
• Molecular Formula: C24H31BrN2O8
• Molecular Weight: 555.423
• Mol file: 478239-48-4.mol

Synonyms:

Chemical Property of 1,2-Pyrrolidinedicarboxylic acid, 5-[(2Z)-2-bromo-4-methoxy-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]- 2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Pyrrolidinedicarboxylic acid, 5-[(2Z)-2-bromo-4-methoxy-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]- 2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,5S)-

There total 4 articles about 1,2-Pyrrolidinedicarboxylic acid, 5-[(2Z)-2-bromo-4-methoxy-4-oxo-3-[[(phenylmethoxy)carbonyl]amino]- 2-butenyl]-, 1-(1,1-dimethylethyl) 2-methyl ester, (2S,5S)- 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: 53.0%

methyl (2S)-cis/trans-(Z)-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-46-2) → methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-47-3) + methyl (2S)-trans-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-48-4)

Guidance literature:

methyl (2S)-cis/trans-(Z)-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate; With N-Bromosuccinimide; In chloroform; at 20 ℃; for 1.33333h;

With 1,4-diaza-bicyclo[2.2.2]octane; In chloroform; at 20 ℃; for 24h; Further stages.;

DOI:10.1021/ol020160a

Reference yield:

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one (108963-96-8) → methyl (2S)-trans-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-48-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LiBEt₃H / tetrahydrofuran / 0.67 h / -78 °C

2.1: p-TsOH / 20 °C

3.1: 1.78 g / BF₃*Et₂O / diethyl ether / 0.25 h / -40 °C

4.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 4 h / 20 °C

5.1: 1.95 g / DBU / CH₂Cl₂ / 8 h / 20 °C

6.1: NBS / CHCl₃ / 1.33 h / 20 °C

6.2: DABCO / CHCl₃ / 24 h / 20 °C

With sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; boron trifluoride diethyl etherate; lithium triethylborohydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; 5.1: Horner-Emmons olefination;

DOI:10.1021/ol020160a

Reference yield:

1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester (188200-05-7) → methyl (2S)-trans-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate (478239-48-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: p-TsOH / 20 °C

2.1: 1.78 g / BF₃*Et₂O / diethyl ether / 0.25 h / -40 °C

3.1: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 4 h / 20 °C

4.1: 1.95 g / DBU / CH₂Cl₂ / 8 h / 20 °C

5.1: NBS / CHCl₃ / 1.33 h / 20 °C

5.2: DABCO / CHCl₃ / 24 h / 20 °C

With sodium periodate; N-Bromosuccinimide; osmium(VIII) oxide; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; 4.1: Horner-Emmons olefination;

DOI:10.1021/ol020160a

upstream raw materials:

methyl (2S)-cis/trans-(Z)-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester

1-tert-butyl 2-methyl (2S)-5-methoxypyrrolidine-1,2-dicarboxylate