3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl ester

Base Information

• Chemical Name: 3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl ester
• CAS No.: 1026578-77-7
• Molecular Formula: C₄₅H₆₀N₆O₁₂
• Molecular Weight: 877.004

Synonyms:3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl ester

Chemical Property of 3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl ester

Chemical Property:

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Technology Process of 3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl ester

There total 10 articles about 3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl 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:

Nα-(tert-butyloxycarbonyl)-D-1-(methoxycarbonyl)tryptophan benzyl ester (136554-90-0) → 3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl ester (1026578-77-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 760 Torr

2: HOBT, EDCI / CH₂Cl₂ / 2 h / Ambient temperature

3: Zn, 90percent AcOH

With hydrogen; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00021a021

Reference yield:

(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester (126090-33-3) → 3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl ester (1026578-77-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NaOH, Bu₄NHSO₄ / CH₂Cl₂ / 4 h / 0 °C

2: 100 percent / H₂ / 10percent Pd/C / methanol; tetrahydrofuran / 760 Torr

3: HOBT, EDCI / CH₂Cl₂ / 2 h / Ambient temperature

4: Zn, 90percent AcOH

With sodium hydroxide; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00021a021

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → 3-[(R)-2-((R)-1-Benzyloxycarbonylmethyl-2-{(S)-2-[(R)-1-((S)-1-carboxy-3-methyl-butylcarbamoyl)-2-methyl-propylcarbamoyl]-pyrrolidin-1-yl}-2-oxo-ethylcarbamoyl)-2-tert-butoxycarbonylamino-ethyl]-indole-1-carboxylic acid methyl ester (1026578-77-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / HOBT, EDCI, NMM / CH₂Cl₂ / 3 h / Ambient temperature

2: TFA / 0.67 h / 0 °C

3: HOBT, EDCI, NMM / CH₂Cl₂ / 2.5 h / Ambient temperature

4: TFA / 1.5 h / Ambient temperature

5: HOBT, EDCI / CH₂Cl₂ / 2 h / Ambient temperature

6: Zn, 90percent AcOH

With 4-methyl-morpholine; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid; zinc; In dichloromethane;

DOI:10.1021/jm00021a021

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

Boc-D-Trp(Nⁱⁿ-COOMe)-OH

Boc-Pro-D-Val-Leu-OPac

(S)-2-((R)-2-{[(S)-1-((R)-2-Amino-3-benzyloxycarbonyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-3-methyl-butyrylamino)-4-methyl-pentanoic acid 2-oxo-2-phenyl-ethyl ester

Downstream raw materials:

H-D-Trp(Nⁱⁿ-COOMe)-D-Asp(OBzl)-Pro-D-Val-Leu-OH

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