N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid

Base Information

• Chemical Name: N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid
• CAS No.: 261919-05-5
• Molecular Formula: C₂₄H₃₀N₂O₆
• Molecular Weight: 442.512
• Mol file: 261919-05-5.mol

Synonyms:N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid

Chemical Property of N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid

There total 8 articles about N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid 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: 71.0%

Z-Leu-OH (2018-66-8) + 3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid (191849-93-1) → N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid (261919-05-5)

Guidance literature:

3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid; With thionyl chloride; In methanol;

Z-Leu-OH; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; In N,N-dimethyl-formamide;

With lithium hydroxide; In methanol;

DOI:10.1016/S0960-894X(01)00526-1

Reference yield:

3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester (261786-25-8) → N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid (261919-05-5)

Guidance literature:

With sodium hydroxide; In methanol; for 1h; Yield given;

DOI:10.1021/jm00044a013

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → N-(Cbz-Leu)-3(S)-amino-2(R,S)-hydroxy-4-phenylbutanoic acid (261919-05-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / CDI, DIEA / tetrahydrofuran; dimethylformamide / Ambient temperature

2: LiAlH₄ / diethyl ether / 0.5 h / 0 - 5 °C

3: 1.) aq. NaHSO₃ / 1.) MeOH, 5 deg C, overnight, 2.) MeOH, H₂O, AcOEt, RT, 5 h

4: conc. aq. HCl, anisole / dioxane / Heating

5: 64 percent / SOCl₂ / Ambient temperature

6: DIEA / tetrahydrofuran; dioxane / Ambient temperature

7: 1 N NaOH / methanol / 1 h

With hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; thionyl chloride; sodium hydrogensulfite; methoxybenzene; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jm00044a013

upstream raw materials:

3(S)-(N-Cbz-leucylamino)-2(R,S)-hydroxy-4-phenylbutanoic acid methyl ester

Z-Leu-OH

3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

[(S)-1-((S)-1-Benzyl-2-hydroxy-2-methoxycarbamoyl-ethylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester