(9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester; hydrochloride

Base Information

• Chemical Name: (9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester; hydrochloride
• CAS No.: 129151-09-3
• Molecular Formula: C₂₈H₂₉N₃O₇*ClH
• Molecular Weight: 556.015

Synonyms:(9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester; hydrochloride

Chemical Property of (9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester; hydrochloride

Chemical Property:

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Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of (9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester; hydrochloride

There total 19 articles about (9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester; hydrochloride 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:

Methyl (9S,12S,15S)-15-<<(1,1-dimethylethoxy)carbonyl>amino>-4-hydroxy-12-<(4-hydroxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.13,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate (120363-26-0) → (9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid methyl ester; hydrochloride (129151-09-3)

Guidance literature:

With hydrogenchloride; In ethyl acetate; at 25 ℃; for 2h;

DOI:10.1021/jo00311a019

Reference yield:

2-Benzyloxycarbonylamino-3-(4-benzyloxy-3-hydroxy-phenyl)-propionic acid methyl ester (105229-41-2) → (9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid methyl ester; hydrochloride (129151-09-3)

Guidance literature:

Multi-step reaction with 15 steps

2: 89 percent / BH₃*THF / tetrahydrofuran / 1) 1 h, 0 deg C 2) to 25 deg C, 2 h

3: 72 percent / CBr₄, Ph₃P / diethyl ether / 6 h / 25 °C

4: 1) NaH / 1) THF, 0 deg C, 10 min 2) hexane, -78 deg C, 14 h

5: 57 percent / 0.5N aq. HCl / tetrahydrofuran / 15 h / 25 °C

6: 97 percent / tetrahydrofuran / 1 h / 25 °C

7: 68 percent / NaH / tetrahydrofuran / 2 h / 25 °C

8: 86 percent / K₂CO₃ / methanol; H₂O / 6 h / 25 °C

9: 91 percent / K₂CO₃ / tetrahydrofuran; H₂O / 2 h / 25 °C

10: 85 percent / EDCI, hydroxybenzotriazol hydrate / CH₂Cl₂ / 9 h / 25 °C

11: 92 percent / n-Bu₄NF / tetrahydrofuran; dimethylformamide / 4 h / 25 °C

12: 85 percent / EDCI / CH₂Cl₂ / 2 h / 25 °C

13: H₂, 10percent aq. HCl / tetrahydrofuran / 4 h / 25 °C / 760 Torr

14: 51 percent / NaHCO₃ / dimethylformamide / 1 h / 90 °C

15: 3.0M HCl / ethyl acetate / 2 h / 25 °C

With hydrogenchloride; borane-THF; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00311a019

Reference yield:

tert-butyl 4-iodobenzoate (120363-13-5) → (9S,12S,15S)-15-Amino-4-hydroxy-12-(4-hydroxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid methyl ester; hydrochloride (129151-09-3)

Guidance literature:

Multi-step reaction with 16 steps

2: 96 percent / 3.0M HCl / ethyl acetate / 1.5 h / 25 °C

3: 89 percent / BH₃*THF / tetrahydrofuran / 1) 1 h, 0 deg C 2) to 25 deg C, 2 h

4: 72 percent / CBr₄, Ph₃P / diethyl ether / 6 h / 25 °C

5: 1) NaH / 1) THF, 0 deg C, 10 min 2) hexane, -78 deg C, 14 h

6: 57 percent / 0.5N aq. HCl / tetrahydrofuran / 15 h / 25 °C

7: 97 percent / tetrahydrofuran / 1 h / 25 °C

8: 68 percent / NaH / tetrahydrofuran / 2 h / 25 °C

9: 86 percent / K₂CO₃ / methanol; H₂O / 6 h / 25 °C

10: 91 percent / K₂CO₃ / tetrahydrofuran; H₂O / 2 h / 25 °C

11: 85 percent / EDCI, hydroxybenzotriazol hydrate / CH₂Cl₂ / 9 h / 25 °C

12: 92 percent / n-Bu₄NF / tetrahydrofuran; dimethylformamide / 4 h / 25 °C

13: 85 percent / EDCI / CH₂Cl₂ / 2 h / 25 °C

14: H₂, 10percent aq. HCl / tetrahydrofuran / 4 h / 25 °C / 760 Torr

15: 51 percent / NaHCO₃ / dimethylformamide / 1 h / 90 °C

16: 3.0M HCl / ethyl acetate / 2 h / 25 °C

With hydrogenchloride; borane-THF; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hydride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00311a019

upstream raw materials:

Methyl (9S,12S,15S)-15-<<(1,1-dimethylethoxy)carbonyl>amino>-4-hydroxy-12-<(4-hydroxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate

sodium 4-iodo-benzoate

tert-butyl 4-iodobenzoate

2-Benzyloxycarbonylamino-3-(4-benzyloxy-3-hydroxy-phenyl)-propionic acid methyl ester

Downstream raw materials:

K-13

Methyl (9S,12S,15S)-15-(acetylamino)-4-hydroxy-12-<(4-hydroxyphenyl)methyl>-11,14-dioxo-2-oxa-10,13-diazatricyclo<15.2.2.1^3,7>docosa-3,5,7(22),17,19,20-hexaene-9-carboxylate

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