(S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester

Base Information

• Chemical Name: (S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester
• CAS No.: 907602-62-4
• Molecular Formula: C₃₆H₄₃BrN₄O₈
• Molecular Weight: 739.663

Synonyms:(S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester

Chemical Property of (S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of (S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester

There total 12 articles about (S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl 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: 75.0%

(S)-(-)-{6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-[3-(4-fluoro-3-nitrophenyl)propionylamino]hexyl}carbamic acid tert-butyl ester (907602-61-3) → (S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester (907602-62-4)

Guidance literature:

With 4 A molecular sieve; cesium fluoride; In dimethyl sulfoxide; at 20 ℃; for 3h;

DOI:10.1021/jm050708u

Reference yield:

3-(4-fluoro-3-nitrophenyl)propionic acid methyl ester (907602-44-2) → (S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester (907602-62-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O

2: 60 mg / HOBt; EDCI / CH₂Cl₂ / 6 h / 20 °C

3: 75 percent / 4 Angstroem sieves; CsF / dimethylsulfoxide / 3 h / 20 °C

With lithium hydroxide; 4 A molecular sieve; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1021/jm050708u

Reference yield:

5-(2-aminoethyl)-2-benzyloxy-3-bromophenol (907602-39-5) → (S)-(-)-[4-(4-benzyloxy-5-bromo-20-nitro-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester (907602-62-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetonitrile / 3 h

1.2: 76 percent / Na₂CO₃ / methanol; H₂O / 12 h / 20 °C

2.1: 95 percent / imidazole / dimethylformamide / 20 °C

3.1: 95 percent / CF₃CO₂H / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 81 percent / HOBt; EDCI / CH₂Cl₂ / 3 h / 20 °C

5.1: tris(2-aminoethyl)amine / CH₂Cl₂ / 0.08 h / 20 °C

6.1: 60 mg / HOBt; EDCI / CH₂Cl₂ / 6 h / 20 °C

7.1: 75 percent / 4 Angstroem sieves; CsF / dimethylsulfoxide / 3 h / 20 °C

With 1H-imidazole; 2,2',2''-triaminotriethylamine; 4 A molecular sieve; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; cesium fluoride; trifluoroacetic acid; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm050708u

upstream raw materials:

(S)-(-)-{6-{2-[4-benzyloxy-3-bromo-5-(triisopropyl-silanyloxy)phenyl]ethylcarbamoyl}-5-[3-(4-fluoro-3-nitrophenyl)propionylamino]hexyl}carbamic acid tert-butyl ester

3-(4-fluoro-3-nitrophenyl)propionic acid methyl ester

5-(2-aminoethyl)-2-benzyloxy-3-bromophenol

[2-(4-benzyloxy-3-bromo-5-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester

Downstream raw materials:

(S)-[4-(20-amino-4-benzyloxy-5-bromo-11,15-dioxo-2-oxa-10,14-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaen-13-yl)butyl]carbamic acid tert-butyl ester

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