(S)-2-[1-Benzyl-2-(tert-butoxycarbonyl)hydrazino]-3-methylbutyric acid

Base Information

• Chemical Name: (S)-2-[1-Benzyl-2-(tert-butoxycarbonyl)hydrazino]-3-methylbutyric acid
• CAS No.: 188777-46-0
• Molecular Formula: C17H25N2O4-
• Molecular Weight: 321.3919
• Nikkaji Number: J1.995.532J
• Mol file: 188777-46-0.mol

Synonyms:(S)-2-[1-Benzyl-2-(tert-butoxycarbonyl)hydrazino]-3-methylbutyric acid

Chemical Property of (S)-2-[1-Benzyl-2-(tert-butoxycarbonyl)hydrazino]-3-methylbutyric acid

Chemical Property:

• Melting Point: 108-112 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 85.19000
• Density: g/cm³
• LogP: 1.90720
• Storage Temp.: 0-6°C
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 322.18925731
• Heavy Atom Count: 23
• Complexity: 398

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)N(CC1=CC=CC=C1)NC(=O)OC(C)(C)C
• Isomeric SMILES: CC(C)[C@@H](C(=O)O)N(CC1=CC=CC=C1)NC(=O)OC(C)(C)C

Technology Process of (S)-2-[1-Benzyl-2-(tert-butoxycarbonyl)hydrazino]-3-methylbutyric acid

There total 7 articles about (S)-2-[1-Benzyl-2-(tert-butoxycarbonyl)hydrazino]-3-methylbutyric 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: 68.0%

(S)-2-(benzylamino)-3-methylbutanoic acid (15363-84-5) + N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine (150884-56-3,158807-35-3) → (S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}-3-methylbutanoic acid (188777-46-0,313672-19-4)

Guidance literature:

With tetraethylammonium hydroxide; 1.) MeOH, 2.) CH₂Cl₂;

DOI:10.1002/chem.19970031019

Reference yield:

N-(tert-butyloxycarbonyl) azide (1070-19-5) → (S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}-3-methylbutanoic acid (188777-46-0,313672-19-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / diethyl ether

2: 75 percent / toluene / 17 h / Heating

3: LiMCPBA / CH₂Cl₂ / 2 h / -78 °C

4: 68 percent / Et₄NOH / 1.) MeOH, 2.) CH₂Cl₂

With LiMCPBA; tetraethylammonium hydroxide; In diethyl ether; dichloromethane; toluene;

DOI:10.1002/chem.19970031019

Reference yield:

triphenyl(t-butoxycarbonylimino)phosphorane (68014-21-1) → (S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}-3-methylbutanoic acid (188777-46-0,313672-19-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / toluene / 17 h / Heating

2: LiMCPBA / CH₂Cl₂ / 2 h / -78 °C

3: 68 percent / Et₄NOH / 1.) MeOH, 2.) CH₂Cl₂

With LiMCPBA; tetraethylammonium hydroxide; In dichloromethane; toluene;

DOI:10.1002/chem.19970031019

upstream raw materials:

(S)-2-(benzylamino)-3-methylbutanoic acid

N-tert-butyloxycarbonyl-3-(4-cyanophenyl)oxaziridine

t-butyl 3-(trichloromethyl)-1,2-oxaziridine-2-carboxylate

L-valine

Downstream raw materials:

(S)-2-(1-benzyl-2-{(S)-2-[1-benzyl-2-((S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}-3-methylbutanoyl)hydrazino]propanoyl}hydrazino)-4-methylpentanoic acid

C₇₆H₁₀₄N₁₂O₉

Boc-NH(Bzl)Val-Ala-Ala-NHⁱPr

methyl (S)-2-(1-benzyl-2-{(S)-2-[1-benzyl-2-((S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}-3-methylbutanoyl)hydrazino]propanoyl}hydrazino)-4-methylpentanoate