1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate

Base Information

• Chemical Name: 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate
• CAS No.: 528588-37-6
• Molecular Formula: C₂₂H₃₂BrNO₆
• Molecular Weight: 486.403
• Mol file: 528588-37-6.mol

Synonyms:1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate

Chemical Property of 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate

There total 3 articles about 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate 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: 72.0%

1-bromomethyl-4-bromobenzene (589-15-1) + (S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate (24277-38-1) → 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate (528588-37-6)

Guidance literature:

(S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

1-bromomethyl-4-bromobenzene; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)02865-4

Reference yield:

N-tert-butoxycarbonyl glutamic acid tert-butyl ester (24277-39-2) → 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate (528588-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 76 percent / DCC / 5 h

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 72 percent / tetrahydrofuran

With dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(02)02865-4

Reference yield:

(2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid (45214-91-3) → 1-tert-butyl 5-methyl (2S,4S)-4-[(4-bromophenyl)methyl]-2-{[(tert-butoxy)carbonyl]amino}pentanedioate (528588-37-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: boron trifluoride diethyl etherate / dichloromethane; cyclohexane / 20 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -70 °C

2.2: 4 h / -70 °C

With boron trifluoride diethyl etherate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; cyclohexane;

upstream raw materials:

1-bromomethyl-4-bromobenzene

(S)-(-)-1-tert-butyl-5-methyl-<(2-tert-butoxycarbonyl)amino>pentanedioate

N-tert-butoxycarbonyl glutamic acid tert-butyl ester

(2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid

Downstream raw materials:

4-(4-bromo-benzyl)-2-tert-butoxycarbonylamino-5-(toluene-4-sulfonyloxy)-pentanoic acid tert-butyl ester

5-(4-bromo-phenyl)-2-tert-butoxycarbonylamino-4-hydroxymethyl-pentanoic acid tert-butyl ester