(S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: (S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 172663-01-3
• Molecular Formula: C₃₈H₅₁IN₄O₅Si
• Molecular Weight: 798.837

Synonyms:

Chemical Property of (S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester

There total 6 articles about (S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl 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:

4-nitro-3-phenyl-L-alanine (949-99-5) → (S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester (172663-01-3)

Guidance literature:

Multi-step reaction with 8 steps

1: aq. NaOH, NaHCO₃ / dioxane / 0 - 20 °C

2: N-methyl morpholine / tetrahydrofuran

3: diethyl ether / 0 - 20 °C

4: silver benzoate, Et₃N

5: 61 percent / H₂ / Pd(OH)2 / ethanol / 2585.7 Torr

6: 74 percent / NaI, chloramine T / acetic acid / 0.75 h / Ambient temperature

7: p-toluenesulfonic acid / CH₂Cl₂ / Ambient temperature

8: 1.) 1-hydroxybenzotriazole, 1,3-dicyclohexylcarbodiimide / 1.) EtOAc, RT, 2.) EtOAc, RT

With 4-methyl-morpholine; sodium hydroxide; hydrogen; chloroamine-T; silver benzoate; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; ethanol; dichloromethane; acetic acid;

DOI:10.1016/0968-0896(96)00185-X

Reference yield:

Boc-Phe(p-NO2)-OH (33305-77-0) → (S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester (172663-01-3)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methyl morpholine / tetrahydrofuran

2: diethyl ether / 0 - 20 °C

3: silver benzoate, Et₃N

4: 61 percent / H₂ / Pd(OH)2 / ethanol / 2585.7 Torr

5: 74 percent / NaI, chloramine T / acetic acid / 0.75 h / Ambient temperature

6: p-toluenesulfonic acid / CH₂Cl₂ / Ambient temperature

7: 1.) 1-hydroxybenzotriazole, 1,3-dicyclohexylcarbodiimide / 1.) EtOAc, RT, 2.) EtOAc, RT

With 4-methyl-morpholine; hydrogen; chloroamine-T; silver benzoate; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; palladium dihydroxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetic acid;

DOI:10.1016/0968-0896(96)00185-X

Reference yield:

(S)-3-tert-butoxycarbonylamino-4-(4-nitrophenyl)butyric acid 2-trimethylsilanyl ethyl ester (151291-13-3) → (S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester (172663-01-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / H₂ / Pd(OH)2 / ethanol / 2585.7 Torr

2: 74 percent / NaI, chloramine T / acetic acid / 0.75 h / Ambient temperature

3: p-toluenesulfonic acid / CH₂Cl₂ / Ambient temperature

4: 1.) 1-hydroxybenzotriazole, 1,3-dicyclohexylcarbodiimide / 1.) EtOAc, RT, 2.) EtOAc, RT

With hydrogen; chloroamine-T; benzotriazol-1-ol; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; sodium iodide; palladium dihydroxide; In ethanol; dichloromethane; acetic acid;

DOI:10.1016/0968-0896(96)00185-X

upstream raw materials:

N-[(2-adamantyloxy)-carbonyl]-α-methyl-R-tryptophane

(S)-3-Amino-4-(4-amino-3-iodo-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester

4-nitro-3-phenyl-L-alanine

Boc-Phe(p-NO₂)-OH

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