(S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid

Base Information

• Chemical Name: (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid
• CAS No.: 357958-48-6
• Molecular Formula: C₂₇H₃₁N₅O₁₂
• Molecular Weight: 617.569
• Mol file: 357958-48-6.mol

Synonyms:

Chemical Property of (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid

There total 12 articles about (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric 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:

(S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-(2-trimethylsilanyl-ethyl) ester (1006729-24-3) → (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid (357958-48-6)

Guidance literature:

Multi-step reaction with 8 steps

1: H⁺

2: TBAF / tetrahydrofuran

3: EDC; HOBt; DMAP / dimethylformamide

4: H₂ / Pd/C

5: EDC; HOBt; DMAP / dimethylformamide

6: TBAF / tetrahydrofuran

7: EDC; HOBt / dimethylformamide

8: TFA; Et₃SH / CH₂Cl₂

With dmap; tetrabutyl ammonium fluoride; hydrogen; hydrogen cation; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00103-2

Reference yield:

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid (23632-67-9) → (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid (357958-48-6)

Guidance literature:

Multi-step reaction with 10 steps

1: EDC; DMAP / CH₂Cl₂

2: NaOH / tetrahydrofuran

3: H⁺

4: TBAF / tetrahydrofuran

5: EDC; HOBt; DMAP / dimethylformamide

6: H₂ / Pd/C

7: EDC; HOBt; DMAP / dimethylformamide

8: TBAF / tetrahydrofuran

9: EDC; HOBt / dimethylformamide

10: TFA; Et₃SH / CH₂Cl₂

With dmap; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; hydrogen cation; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00103-2

Reference yield:

(S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester (203919-89-5) → (S)-4-[(S)-1-Carboxy-2-(4-hydroxy-3-nitro-phenyl)-ethylcarbamoyl]-2-[(S)-4-carboxy-4-(4-methylamino-benzoylamino)-butyrylamino]-butyric acid (357958-48-6)

Guidance literature:

Multi-step reaction with 9 steps

1: NaOH / tetrahydrofuran

2: H⁺

3: TBAF / tetrahydrofuran

4: EDC; HOBt; DMAP / dimethylformamide

5: H₂ / Pd/C

6: EDC; HOBt; DMAP / dimethylformamide

7: TBAF / tetrahydrofuran

8: EDC; HOBt / dimethylformamide

9: TFA; Et₃SH / CH₂Cl₂

With dmap; sodium hydroxide; tetrabutyl ammonium fluoride; hydrogen; hydrogen cation; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(01)00103-2

upstream raw materials:

(S)-2-(benzyloxycarbonylamino)pentanedioic acid tert-butyl ester

(S)-3-[3-(benzyloxycarbonyl)-5-oxooxazolidin-4-yl]propanoic acid

(S)-5-Oxo-4-[2-(2-trimethylsilanyl-ethoxycarbonyl)-ethyl]-oxazolidine-3-carboxylic acid benzyl ester

H-Glu(α-OtBu)(γ-OTMSE)

Downstream raw materials:

p-(N-methylamino)benzoyl-L-glutamic acid