N^α-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl ester

Base Information

• Chemical Name: N^α-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl ester
• CAS No.: 174359-58-1
• Molecular Formula: C₃₂H₃₅N₅O₉
• Molecular Weight: 633.658

Synonyms:N^α-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl ester

Chemical Property of N^α-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl ester

Chemical Property:

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Technology Process of N^α-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl ester

There total 8 articles about N^α-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl 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: 78.0%

N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine (152120-55-3) + Nα-(tert-butyloxycarbonyl)glycylglycine p-aminophenyl ester → Nα-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl ester (174359-58-1)

Guidance literature:

In tetrahydrofuran; Ambient temperature;

DOI:10.1248/cpb.43.2082

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → Nα-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl ester (174359-58-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 74 percent / TsOH*H₂O / benzene / 0.5 h / 60 °C

2: H₂ / 10percent Pd/C / ethanol / 20 h / Ambient temperature

3: CHCl₃ / 2 h / Ambient temperature

4: 97 percent / TsOH*H₂O / methanol / 1 h / Heating

5: 66 percent / DMAP, DCC / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

6: H₂ / 10percent Pd/C / ethanol / Ambient temperature

7: 78 percent / tetrahydrofuran / Ambient temperature

With dmap; hydrogen; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.43.2082

Reference yield:

2-(4-nitrophenoxy)tetrahydropyran (20443-91-8) → Nα-(tert-butyloxycarbonyl)glycylglycine p-(N',N''-bis(benzyloxycarbonyl)guanidino)phenyl ester (174359-58-1)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / 10percent Pd/C / ethanol / 20 h / Ambient temperature

2: CHCl₃ / 2 h / Ambient temperature

3: 97 percent / TsOH*H₂O / methanol / 1 h / Heating

4: 66 percent / DMAP, DCC / CH₂Cl₂; dimethylformamide / 1 h / 0 °C

5: H₂ / 10percent Pd/C / ethanol / Ambient temperature

6: 78 percent / tetrahydrofuran / Ambient temperature

With dmap; hydrogen; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1248/cpb.43.2082

upstream raw materials:

N,N-bis(benzyloxycarbonyl)-1H-pyrazole-1-carboxamidine

4-nitro-phenol

2-(4-nitrophenoxy)tetrahydropyran

Boc-Gly-Gly-OH

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