(2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER

Base Information

• Chemical Name: (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER
• CAS No.: 487048-27-1
• Molecular Formula: C₁₄H₂₄BrNO₄
• Molecular Weight: 350.253
• Mol file: 487048-27-1.mol

Synonyms:(2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER

Chemical Property of (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER

Chemical Property:

• Vapor Pressure: 8.87E-06mmHg at 25°C
• Refractive Index: 1.503
• Boiling Point: 373.6°Cat760mmHg
• Flash Point: 179.7°C
• PSA: 55.84000
• Density: 1.304g/cm³
• LogP: 3.03890

Purity/Quality:

95% ^*data from raw suppliers

(2S)-N-BOC-CIS-4-BROMO-L-PROLINE TERT-BUTYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-BUTYL ESTER

There total 4 articles about (2S)-N-BOC-CIS-4-BROMO-L-PROLINE T-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: 74.0%

BOC-Hyp-OtBu (170850-75-6) → (2S)-N-Boc-cis-4-bromo-L-proline tert-butyl ester (487048-27-1)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1021/jo050838a

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2S)-N-Boc-cis-4-bromo-L-proline tert-butyl ester (487048-27-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / Na₂CO₃ / H₂O; dioxane

2: 80 percent / tetrahydrofuran / 20 - 60 °C

3: 74 percent / tetrabromomethane; triphenylphosphine / CH₂Cl₂ / 15 h / 20 °C

With carbon tetrabromide; sodium carbonate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; 3: Mitsunobu bromination;

DOI:10.1021/jo050838a

Reference yield:

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid (13726-69-7,946610-68-0) → (2S)-N-Boc-cis-4-bromo-L-proline tert-butyl ester (487048-27-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / tetrahydrofuran / 20 - 60 °C

2: 74 percent / tetrabromomethane; triphenylphosphine / CH₂Cl₂ / 15 h / 20 °C

With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; dichloromethane; 2: Mitsunobu bromination;

DOI:10.1021/jo050838a

upstream raw materials:

BOC-Hyp-OtBu

di-tert-butyl dicarbonate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

4R-4-hydroxyproline

Downstream raw materials:

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

Refernces