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

Base Information

• Chemical Name: phenylmethyl (2R,5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methylamino)carbonyl]-1-pyrrolidinecarboxylate
• CAS No.: 1070868-59-5
• Molecular Formula: C₃₄H₄₃FN₂O₅Si
• Molecular Weight: 606.81
• Mol file: 1070868-59-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about phenylmethyl (2R,5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methylamino)carbonyl]-1-pyrrolidinecarboxylate 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: 71.3%

(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) + methylamine (74-89-5) → phenylmethyl (2R,5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methylamino)carbonyl]-1-pyrrolidinecarboxylate (1070868-59-5)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 1h;

Reference yield:

o-fluorobenzyl bromide (446-48-0) → phenylmethyl (2R,5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methylamino)carbonyl]-1-pyrrolidinecarboxylate (1070868-59-5)

Guidance literature:

Multi-step reaction with 10 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

10.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; hydrogen; iodine; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; magnesium; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; citric acid; lithium hexamethyldisilazane; platinum on carbon; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone;

Reference yield:

1-[(4-bromophenoxy)methyl]-2-fluorobenzene (934240-59-2) → phenylmethyl (2R,5R)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-[(methylamino)carbonyl]-1-pyrrolidinecarboxylate (1070868-59-5)

Guidance literature:

Multi-step reaction with 9 steps

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

1.2: 2.25 h / -60 °C

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

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

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

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

5.2: 7 h / -78 °C

6.1: 2,6-dimethylpyridine / dichloromethane / 3 h / 0 - 20 °C

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

8.1: citric acid / water / pH 5

9.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; hydrogen; iodine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; magnesium; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; citric acid; lithium hexamethyldisilazane; platinum on carbon; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

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

methylamine

o-fluorobenzyl bromide

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

Downstream raw materials:

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

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

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