(S)-1-[(R)-4-((S)-5-Amino-2-benzyloxycarbonylamino-pentanoylamino)-4-carboxy-butyryl]-2,3-dihydro-1H-indole-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-[(R)-4-((S)-5-Amino-2-benzyloxycarbonylamino-pentanoylamino)-4-carboxy-butyryl]-2,3-dihydro-1H-indole-2-carboxylic acid
• CAS No.: 116587-00-9
• Molecular Formula: C₂₇H₃₂N₄O₈
• Molecular Weight: 540.573
• Mol file: 116587-00-9.mol

Synonyms:

Chemical Property of (S)-1-[(R)-4-((S)-5-Amino-2-benzyloxycarbonylamino-pentanoylamino)-4-carboxy-butyryl]-2,3-dihydro-1H-indole-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(R)-4-((S)-5-Amino-2-benzyloxycarbonylamino-pentanoylamino)-4-carboxy-butyryl]-2,3-dihydro-1H-indole-2-carboxylic acid

There total 7 articles about (S)-1-[(R)-4-((S)-5-Amino-2-benzyloxycarbonylamino-pentanoylamino)-4-carboxy-butyryl]-2,3-dihydro-1H-indole-2-carboxylic 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:

Ethyl (S)-indoline-2-carboxylate hydrochloride (79854-42-5) → (S)-1-[(R)-4-((S)-5-Amino-2-benzyloxycarbonylamino-pentanoylamino)-4-carboxy-butyryl]-2,3-dihydro-1H-indole-2-carboxylic acid (116587-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / EDC*HCl, triethylamine / CH₂Cl₂ / 5 h

2: 81 percent / H₂ / 5percent Pd/C / methanol; acetic acid / 2 h

3: EDC*HCl / CH₂Cl₂

4: 1N NaOH / ethanol / 1.5 h

5: TFA / 0.5 h

With sodium hydroxide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid;

DOI:10.1248/cpb.37.2417

Reference yield:

ethyl 1-<4-(N-carbobenzoxyamino)-4-carboethoxy-4(R)-butyryl>indoline-2(S)-carboxylic acid (97975-53-6) → (S)-1-[(R)-4-((S)-5-Amino-2-benzyloxycarbonylamino-pentanoylamino)-4-carboxy-butyryl]-2,3-dihydro-1H-indole-2-carboxylic acid (116587-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / H₂ / 5percent Pd/C / methanol; acetic acid / 2 h

2: EDC*HCl / CH₂Cl₂

3: 1N NaOH / ethanol / 1.5 h

4: TFA / 0.5 h

With sodium hydroxide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid;

DOI:10.1248/cpb.37.2417

Reference yield:

α-ethyl D-N-carbobenzoxyglutamate (97996-97-9) → (S)-1-[(R)-4-((S)-5-Amino-2-benzyloxycarbonylamino-pentanoylamino)-4-carboxy-butyryl]-2,3-dihydro-1H-indole-2-carboxylic acid (116587-00-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 70 percent / EDC*HCl, triethylamine / CH₂Cl₂ / 5 h

2: 81 percent / H₂ / 5percent Pd/C / methanol; acetic acid / 2 h

3: EDC*HCl / CH₂Cl₂

4: 1N NaOH / ethanol / 1.5 h

5: TFA / 0.5 h

With sodium hydroxide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; acetic acid;

DOI:10.1248/cpb.37.2417

upstream raw materials:

Z-Orn(Boc)-OH

Ethyl (S)-indoline-2-carboxylate hydrochloride

ethyl 1-(O¹-ethyl-γ-D-glutamyl)indoline-2(S)-carboxylate

ethyl 1-<4-(N-carbobenzoxyamino)-4-carboethoxy-4(R)-butyryl>indoline-2(S)-carboxylic acid