tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester

Base Information

• Chemical Name: tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester
• CAS No.: 16257-35-5
• Molecular Formula: C₂₁H₃₃N₃O₅
• Molecular Weight: 407.51
• Mol file: 16257-35-5.mol

Synonyms:tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester

Chemical Property of tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester

There total 6 articles about tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester 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: 88.0%

methyl (L)-leucinate hydrochloride (7517-19-3) + L-N-(tert-butoxycarbonylamino)phenylalanine (16257-32-2) → tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester (16257-35-5)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90205-4

Reference yield:

D-phenyllactic acid (828-01-3,7326-19-4,20312-36-1,156-05-8) → tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester (16257-35-5)

Guidance literature:

Multi-step reaction with 4 steps

1: ethyl acetate; diethyl ether

2: 1) Tf₂O, 2,6-lutidine / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, r.t., 3 h

3: 130 mg / 1N NaOH / methanol / 2 h / Ambient temperature

4: 88 percent / NEt₃, HOBT, EDC / tetrahydrofuran / 2 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; trifluoromethylsulfonic anhydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate;

DOI:10.1016/S0040-4020(01)90205-4

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → tert.-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionyl-Leu-methylester (16257-35-5)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂O, NaNO₂, 1 N aq. H₂SO₄ / H₂O / Ambient temperature

2: ethyl acetate; diethyl ether

3: 1) Tf₂O, 2,6-lutidine / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, r.t., 3 h

4: 130 mg / 1N NaOH / methanol / 2 h / Ambient temperature

5: 88 percent / NEt₃, HOBT, EDC / tetrahydrofuran / 2 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; trifluoromethylsulfonic anhydride; sulfuric acid; water; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; sodium nitrite; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate;

DOI:10.1016/S0040-4020(01)90205-4

upstream raw materials:

(S)-Leu-OMe

tert-Butyloxycarbonyl-L-α-hydrazino-β-phenyl-propionsaeure-(N-hydroxy-succinimidester)

methyl (L)-leucinate hydrochloride

L-N-(tert-butoxycarbonylamino)phenylalanine