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,5R)-

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,5R)-
CAS No.:478239-47-3
Molecular Formula:C24H31BrN2O8
Molecular Weight:555.423
Hs Code.:

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,5R)-

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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,5R)-

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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,5R)-

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,5R)- 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%

: 478239-46-2
methyl (2S)-cis/trans-(Z)-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

: 478239-47-3
methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

: 478239-48-4
methyl (2S)-trans-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

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:

: 108963-96-8
(S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one

: 478239-47-3
methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

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: 53 percent / 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:

: 188200-05-7
1-(tertbutyloxycarbonyl)-5-(hydroxy)pyrrolidine-2-carboxylic acid methyl ester

: 478239-47-3
methyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[2'-bromo-(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl] prolinate

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: 53 percent / 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