(R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester

Base Information

• Chemical Name: (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester
• CAS No.: 191664-17-2
• Molecular Formula: C₂₃H₃₆N₂O₅
• Molecular Weight: 420.549
• Mol file: 191664-17-2.mol

Synonyms:(R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester

Chemical Property of (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester

There total 5 articles about (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl 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: 91.0%

(R)-2-{[(tert-butoxycarbonyl)amino]methyl}propionic acid (132696-45-8) + benzyl (2R)-2-aminomethyl4methylpentanoate toluenesulfonate → (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester (191664-17-2)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; 1h, 0 deg C; 18 h, r.t.;

DOI:10.1002/hlca.19980810513

Reference yield:

(S)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one (113543-30-9) → (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester (191664-17-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / TiCl₄, Et₃N / CH₂Cl₂ / 60 h / 0 °C

2: 76 percent / H₂O₂, LiOH*H₂O / H₂O; tetrahydrofuran / 1 h / 0 °C

3: 65 percent / aq. HCl / acetic acid / 48 h / Heating

4: 86 percent / benzene / 9 h / Heating

5: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; dihydrogen peroxide; titanium tetrachloride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetic acid; benzene;

DOI:10.1002/hlca.19980810513

Reference yield:

N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-4-methyl-pentyl]-benzamide (191664-13-8) → (R)-2-[((R)-3-tert-Butoxycarbonylamino-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester (191664-17-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / H₂O₂, LiOH*H₂O / H₂O; tetrahydrofuran / 1 h / 0 °C

2: 65 percent / aq. HCl / acetic acid / 48 h / Heating

3: 86 percent / benzene / 9 h / Heating

4: 91 percent / 1-hydroxy-1H-benzotriazole, N-methylmorpholine, 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide / tetrahydrofuran / 1h, 0 deg C; 18 h, r.t.

With 4-methyl-morpholine; hydrogenchloride; lithium hydroxide; dihydrogen peroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; water; acetic acid; benzene;

DOI:10.1002/hlca.19980810513

upstream raw materials:

(R)-2-{[(tert-butoxycarbonyl)amino]methyl}propionic acid

(S)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one

(2R)-([amino]methyl)-4-methylpentanoic acid

N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-4-methyl-pentyl]-benzamide

Downstream raw materials:

(R)-2-({(R)-3-[(R)-2-(tert-Butoxycarbonylamino-methyl)-3-methyl-butyrylamino]-2-methyl-propionylamino}-methyl)-4-methyl-pentanoic acid benzyl ester

C₄₆H₇₈N₆O₉

(R)-2-[((R)-3-{(R)-2-[((2R,3R)-3-tert-Butoxycarbonylamino-2-methyl-butyrylamino)-methyl]-3-methyl-butyrylamino}-2-methyl-propionylamino)-methyl]-4-methyl-pentanoic acid benzyl ester

Boc-(R)-β²-HVal-(R)-β²-HAla-(R)-β²-HLeu-(2R,3R)-β^2,3-HAla(α-Me)-(R)-β²-HVal-(R)-β²-HAla-(R)-β²-HLeu-OBn