(S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic acid

Base Information

• Chemical Name: (S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic acid
• CAS No.: 107327-09-3
• Molecular Formula: C₂HF₃O₂*C₅₀H₆₇N₉O₁₁
• Molecular Weight: 1084.16

Synonyms:(S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic acid

Chemical Property of (S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic acid

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Technology Process of (S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic acid

There total 7 articles about (S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic 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: 88.0%

Boc-Tyr-Nle-D-Lys(Z)-Trp-Nle-Asp-NH2 (107326-94-3) + trifluoroacetic acid (76-05-1) → (S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic acid (107327-09-3)

Guidance literature:

With methoxybenzene; In dichloromethane; at 0 - 20 ℃; for 1.5h;

DOI:10.1021/jm00389a002

Reference yield:

Boc-Tyr-OH (3978-80-1) → (S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic acid (107327-09-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / Et₃N, 1-hydroxybenzotriazole (HOBt), N,N'-dicyclohexylcarbodiimide (DCC) / CHCl₃ / a) 0 deg C, 1 h, b) RT, overnight

2: 82 percent / 1N NaOH / methanol / Ambient temperature

3: 1.) N-hydroxysuccinimide (HONSu), N,N'-dicyclohexylcarbodiimide (DCC), 2.) Et₃N / 1.) DMF a) from -10 deg C to 0 deg C, 2 h 45 min, b) RT, overnight, 2.) DMF, RT, 48 h

4: 88 percent / anisole / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; benzotriazol-1-ol; methoxybenzene; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; chloroform;

DOI:10.1021/jm00389a002

Reference yield:

H-Nle-Asp-NH2 (106637-14-3) → (S)-3-{(S)-2-[(S)-2-((R)-2-{(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-hexanoylamino}-6-benzyloxycarbonylamino-hexanoylamino)-3-(1H-indol-3-yl)-propionylamino]-hexanoylamino}-succinamic acid; compound with trifluoro-acetic acid (107327-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) N-hydroxysuccinimide (HONSu), N,N'-dicyclohexylcarbodiimide (DCC), 2.) Et₃N / 1.) DMF a) from -10 deg C to 0 deg C, 2 h 45 min, b) RT, overnight, 2.) DMF, RT, 48 h

2: 88 percent / anisole / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; methoxybenzene; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane;

DOI:10.1021/jm00389a002

upstream raw materials:

Boc-Tyr-Nle-D-Lys(Z)-Trp-Nle-Asp-NH₂

trifluoroacetic acid

Boc-Tyr-OH

H-Nle-Asp-NH₂

Downstream raw materials:

Boc-Asp(OBzl)-Tyr-Nle-D-Lys(Z)-Trp-Nle-Asp-NH₂

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