(S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-nitro-phenyl)-butyric acid

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Chemical Name:(S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-nitro-phenyl)-butyric acid
CAS No.:159630-66-7
Molecular Formula:C₃₃H₃₈N₄O₇
Molecular Weight:602.687
Hs Code.:

Synonyms:(S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-nitro-phenyl)-butyric acid

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

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

There total 8 articles about (S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-nitro-phenyl)-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:

: 159630-65-6
(S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-nitro-phenyl)-butyric acid 2-trimethylsilanyl-ethyl ester

: 159630-66-7
(S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-nitro-phenyl)-butyric acid

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;
DOI:10.1016/0968-0896(96)00185-X

Reference yield:

: 949-99-5
4-nitro-3-phenyl-L-alanine

: 159630-66-7
(S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-nitro-phenyl)-butyric acid

Guidance literature:: Multi-step reaction with 7 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: p-toluenesulfonic acid / CH₂Cl₂ / Ambient temperature

6: 1.) 1-hydroxybenzotriazole, 1,3-dicyclohexylcarbodiimide / 1.) EtOAc, RT, 2.) EtOAc, RT

7: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

With 4-methyl-morpholine; sodium hydroxide; tetrabutyl ammonium fluoride; silver benzoate; sodium hydrogencarbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane;
DOI:10.1016/0968-0896(96)00185-X

Reference yield:

: 33305-77-0
Boc-Phe(p-NO₂)-OH

: 159630-66-7
(S)-3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(4-nitro-phenyl)-butyric acid

Guidance literature:: Multi-step reaction with 6 steps

1: N-methyl morpholine / tetrahydrofuran

2: diethyl ether / 0 - 20 °C

3: silver benzoate, Et₃N

4: p-toluenesulfonic acid / CH₂Cl₂ / Ambient temperature

5: 1.) 1-hydroxybenzotriazole, 1,3-dicyclohexylcarbodiimide / 1.) EtOAc, RT, 2.) EtOAc, RT

6: tetrabutylammonium fluoride / tetrahydrofuran / Ambient temperature

With 4-methyl-morpholine; tetrabutyl ammonium fluoride; silver benzoate; benzotriazol-1-ol; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/0968-0896(96)00185-X