(5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline

Base Information

• Chemical Name: (5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline
• CAS No.: 934585-19-0
• Molecular Formula: C₃₃H₄₀FNO₆Si
• Molecular Weight: 593.768
• Mol file: 934585-19-0.mol

Synonyms:(5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline

Chemical Property of (5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline

There total 12 articles about (5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline 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: 83.0%

C33H39FNO6Si(1-)*Li(1+) → (5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline (934585-19-0)

Guidance literature:

With citric acid; In water; pH=5;

Reference yield: 67.0%

→ (5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline (934585-19-0)

Guidance literature:

Reference yield:

o-fluorobenzyl bromide (446-48-0) → (5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-{[(phenylmethyl)oxy]carbonyl}-L-proline (934585-19-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium carbonate / acetone / 2 h / Heating / reflux

2.1: iodine; magnesium / tetrahydrofuran / 1 h / 20 - 65 °C / Heating / reflux

2.2: 2.25 h / -60 °C

3.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

4.1: hydrogen / platinum on carbon / ethyl acetate / 1.5 h / 1520.1 Torr

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 - 20 °C

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.67 h / -78 - -40 °C

6.2: 7 h / -78 °C

7.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C

8.1: lithium hydroxide / methanol; water / 2 h / 90 °C / Microwave irradiation

9.1: citric acid / water / pH 5

With 2,6-dimethylpyridine; lithium hydroxide; hydrogen; iodine; potassium carbonate; magnesium; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; citric acid; lithium hexamethyldisilazane; platinum on carbon; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone;

upstream raw materials:

o-fluorobenzyl bromide

1-[(4-bromophenoxy)methyl]-2-fluorobenzene

methyl (S)-5-(4-((2-fluorobenzyl)oxy)phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

(2S,5R)-methyl-5-(4-((2-fluorobenzyl)oxy)phenyl)pyrrolidine-2-carboxylate

Downstream raw materials:

phenylmethyl (2R,5R)-2-[(dimethylamino)carbonyl]-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-pyrrolidinecarboxylate

phenylmethyl (2R,5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methylamino)carbonyl]-1-pyrrolidinecarboxylate

(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N,N-dimethyl-L-prolinamide

(5R)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-(hydroxymethyl)-N-methyl-L-prolinamide