(8R,11R,14S)-8-Amino-18,19-dichloro-11-(4-hydroxy-phenyl)-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester; hydrobromide

Base Information

• Chemical Name: (8R,11R,14S)-8-Amino-18,19-dichloro-11-(4-hydroxy-phenyl)-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester; hydrobromide
• CAS No.: 127526-61-8
• Molecular Formula: BrH*C₂₇H₂₄Cl₂IN₃O₇
• Molecular Weight: 781.226

Synonyms:

Chemical Property of (8R,11R,14S)-8-Amino-18,19-dichloro-11-(4-hydroxy-phenyl)-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester; hydrobromide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R,11R,14S)-8-Amino-18,19-dichloro-11-(4-hydroxy-phenyl)-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester; hydrobromide

There total 6 articles about (8R,11R,14S)-8-Amino-18,19-dichloro-11-(4-hydroxy-phenyl)-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester; hydrobromide 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:

(11R,14S)-8-Benzyloxycarbonylamino-11-(4-benzyloxy-phenyl)-18,19-dichloro-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid methyl ester → (8R,11R,14S)-8-Amino-18,19-dichloro-11-(4-hydroxy-phenyl)-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid methyl ester; hydrobromide (127526-61-8)

Guidance literature:

With hydrogen bromide; methoxybenzene; In acetic acid; for 8.5h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(01)93850-X

Reference yield:

L-N-(tert-butoxycarbonyl)-4-benzyloxyphenylglycine (123593-66-8) → (8R,11R,14S)-8-Amino-18,19-dichloro-11-(4-hydroxy-phenyl)-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid methyl ester; hydrobromide (127526-61-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) DCC, 1-hydroxybenzotriazol, N-methylmorpholine; 2.) 2N HCl / 1.) DMF, 0 deg C to room temp., overnight; 2.) dioxane, room temp., 4,5 h

2: 1.) DCC, 1-hydroxybenzotriazol, N-methylmorpholine; 2.) 0.05N HCl / 1.) DMF, 0 deg C to room temp., overnight; 2.) MeOH, room temp., 1,5 h

3: 40 percent / TTN / ethyl acetate; tetrahydrofuran; methanol / 2 h / 0 - 4 °C

4: 100 percent / methanol / 1 h / Ambient temperature

5: 30percent HBr, anisole / acetic acid / 8.5 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; hydrogen bromide; benzotriazol-1-ol; methoxybenzene; dicyclohexyl-carbodiimide; thallium(III) nitrate; In tetrahydrofuran; methanol; acetic acid; ethyl acetate;

DOI:10.1016/S0040-4039(01)93850-X

Reference yield:

(S)-2-[(R)-2-Amino-2-(4-benzyloxy-phenyl)-acetylamino]-3-(3,5-dichloro-4-hydroxy-phenyl)-propionic acid methyl ester; hydrochloride (127526-60-7) → (8R,11R,14S)-8-Amino-18,19-dichloro-11-(4-hydroxy-phenyl)-5-iodo-4-methoxy-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid methyl ester; hydrobromide (127526-61-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) DCC, 1-hydroxybenzotriazol, N-methylmorpholine; 2.) 0.05N HCl / 1.) DMF, 0 deg C to room temp., overnight; 2.) MeOH, room temp., 1,5 h

2: 40 percent / TTN / ethyl acetate; tetrahydrofuran; methanol / 2 h / 0 - 4 °C

3: 100 percent / methanol / 1 h / Ambient temperature

4: 30percent HBr, anisole / acetic acid / 8.5 h / Ambient temperature

With 4-methyl-morpholine; hydrogenchloride; hydrogen bromide; benzotriazol-1-ol; methoxybenzene; dicyclohexyl-carbodiimide; thallium(III) nitrate; In tetrahydrofuran; methanol; acetic acid; ethyl acetate;

DOI:10.1016/S0040-4039(01)93850-X

upstream raw materials:

L-N-(tert-butoxycarbonyl)-4-benzyloxyphenylglycine

(S)-2-[(R)-2-Amino-2-(4-benzyloxy-phenyl)-acetylamino]-3-(3,5-dichloro-4-hydroxy-phenyl)-propionic acid methyl ester; hydrochloride

(11R,14S)-8-Benzyloxycarbonylamino-11-(4-benzyloxy-phenyl)-18,19-dichloro-4-hydroxy-5-iodo-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

(S)-2-[(R)-2-[(R)-2-Benzyloxycarbonylamino-2-(4-hydroxy-3,5-diiodo-phenyl)-acetylamino]-2-(4-benzyloxy-phenyl)-acetylamino]-3-(3,5-dichloro-4-hydroxy-phenyl)-propionic acid methyl ester

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