(S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.0^6,11]hexacosa-6⁽¹¹⁾,7,9,22,24-pentaene-3,26-dione

Base Information

• Chemical Name: (S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.0^6,11]hexacosa-6⁽¹¹⁾,7,9,22,24-pentaene-3,26-dione
• CAS No.: 496917-19-2
• Molecular Formula: C₂₇H₃₁Cl₂N₅O₃
• Molecular Weight: 544.481

Synonyms:(S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.0^6,11]hexacosa-6⁽¹¹⁾,7,9,22,24-pentaene-3,26-dione

Chemical Property of (S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.0^6,11]hexacosa-6⁽¹¹⁾,7,9,22,24-pentaene-3,26-dione

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Technology Process of (S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.0^6,11]hexacosa-6⁽¹¹⁾,7,9,22,24-pentaene-3,26-dione

There total 10 articles about (S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.0^6,11]hexacosa-6⁽¹¹⁾,7,9,22,24-pentaene-3,26-dione 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:

[3-(1-{[5-(2-aminomethyl-4-chloro-phenoxy)-pentylamino]-methyl}-2-phenyl-ethylamino)-6-chloro-2-oxo-2H-pyrazin-1-yl]-acetic acid → (S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.06,11]hexacosa-6(11),7,9,22,24-pentaene-3,26-dione (496917-19-2)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In N,N-dimethyl-formamide; at 50 ℃;

DOI:10.1016/S0040-4039(03)00216-8

Reference yield:

[3-(1-azidomethyl-2-phenyl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester (450416-15-6) → (S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.06,11]hexacosa-6(11),7,9,22,24-pentaene-3,26-dione (496917-19-2)

Guidance literature:

Multi-step reaction with 6 steps

1: NCS; DCE / 80 °C

2: SnCl₂ / methanol

3: NaBH(OAc)3; DCE

4: HCl / CH₂Cl₂

5: aq. LiOH / tetrahydrofuran

6: EDC; HOAt; Et₃N / dimethylformamide

With hydrogenchloride; lithium hydroxide; N-chloro-succinimide; 1-hydroxy-7-aza-benzotriazole; DCE; sodium tris(acetoxy)borohydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; tin(ll) chloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00506-7

Reference yield:

[3-(1-aminomethyl-2-phenyl-ethylamino)-6-chloro-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester (450416-18-9) → (S)-20-Benzyl-8,25-dichloro-12-oxa-1,4,18,21,23-pentaaza-tricyclo[20.3.1.06,11]hexacosa-6(11),7,9,22,24-pentaene-3,26-dione (496917-19-2)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH(OAc)3; DCE

2: HCl / CH₂Cl₂

3: aq. LiOH / tetrahydrofuran

4: EDC; HOAt; Et₃N / dimethylformamide

With hydrogenchloride; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; DCE; sodium tris(acetoxy)borohydride; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(03)00506-7

upstream raw materials:

(S)-1-azido-3-phenylpropan-2-amine

ethyl 2-[3-bromo-2-oxo-1(2H)-pyrazinyl]acetate

[3-(1-azidomethyl-2-phenyl-ethylamino)-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester

[3-(1-aminomethyl-2-phenyl-ethylamino)-6-chloro-2-oxo-2H-pyrazin-1-yl]-acetic acid ethyl ester

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