3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(2,6-dichloro-phenyl)-butyric acid ethyl ester

Base Information

• Chemical Name: 3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(2,6-dichloro-phenyl)-butyric acid ethyl ester
• CAS No.: 185321-46-4
• Molecular Formula: C₃₅H₄₁Cl₂N₃O₅
• Molecular Weight: 654.634
• Mol file: 185321-46-4.mol

Synonyms:

Chemical Property of 3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(2,6-dichloro-phenyl)-butyric acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(2,6-dichloro-phenyl)-butyric acid ethyl ester

There total 4 articles about 3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(2,6-dichloro-phenyl)-butyric acid 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:

2'-chloro-benzeneacetic acid (2444-36-2) → 3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(2,6-dichloro-phenyl)-butyric acid ethyl ester (185321-46-4)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / 16 h / 0 - 20 °C

2: tetrahydrofuran; acetonitrile / 16 h / Ambient temperature

3: 1.) NH₄OAc, molecular sieves 3A, 2.) NaBH₃CN, HCl / 1.) MeOH, RT, 1 week, 2.) MeOH, RT, 16 h

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

With hydrogenchloride; 3 A molecular sieve; ammonium acetate; sodium cyanoborohydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; acetonitrile;

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

Reference yield:

(2-Chloro-phenyl)-acetic acid imidazol-1-yl ester → 3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(2,6-dichloro-phenyl)-butyric acid ethyl ester (185321-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; acetonitrile / 16 h / Ambient temperature

2: 1.) NH₄OAc, molecular sieves 3A, 2.) NaBH₃CN, HCl / 1.) MeOH, RT, 1 week, 2.) MeOH, RT, 16 h

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

With hydrogenchloride; 3 A molecular sieve; ammonium acetate; sodium cyanoborohydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; acetonitrile;

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

Reference yield:

4-(2-Chloro-phenyl)-3-oxo-butyric acid ethyl ester (83657-82-3) → 3-[(R)-2-(Adamantan-2-yloxycarbonylamino)-3-(1H-indol-3-yl)-2-methyl-propionylamino]-4-(2,6-dichloro-phenyl)-butyric acid ethyl ester (185321-46-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) NH₄OAc, molecular sieves 3A, 2.) NaBH₃CN, HCl / 1.) MeOH, RT, 1 week, 2.) MeOH, RT, 16 h

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

With hydrogenchloride; 3 A molecular sieve; ammonium acetate; sodium cyanoborohydride; benzotriazol-1-ol; dicyclohexyl-carbodiimide;

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

upstream raw materials:

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

3-amino-4-(2-chlorophenyl)butyric acid ethyl ester

2'-chloro-benzeneacetic acid

4-(2-Chloro-phenyl)-3-oxo-butyric acid ethyl ester