[15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid

Base Information

• Chemical Name: [15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid
• CAS No.: 371111-92-1
• Molecular Formula: C₃₁H₃₉N₃O₇
• Molecular Weight: 565.667

Synonyms:[15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid

Chemical Property of [15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid

Chemical Property:

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Useful:

Technology Process of [15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid

There total 4 articles about [15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3⁽²²⁾,4,6,17⁽²¹⁾,18-hexaene-9-carboxylic acid 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:

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester (371111-41-0) → [15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid (371111-92-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / HCl / dioxane / 2 h / 20 °C

With hydrogenchloride; In 1,4-dioxane;

DOI:10.1021/jm0489556

Reference yield:

N-(tert-butoxycarbonyl)-L-cyclohexylglycine (109183-71-3) → [15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid (371111-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 4-methylmorpholine; isobutyl chloroformate / CH₂Cl₂ / -10 - -5 °C

1.2: 53 percent / 4-methylmorpholine / CH₂Cl₂; dimethylformamide / 1 h / 20 °C

2.1: 96 percent / HCl / dioxane / 2 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; isobutyl chloroformate; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm0489556

Reference yield:

methyl (2S)-2-amino-3-(3-hydroxyphenyl)propanoate hydrochloride (34260-70-3,34260-72-5,72683-79-5) → [15S,12S,9S]-15-tert-butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[15.2.2.13,7]docosa-1(20),3(22),4,6,17(21),18-hexaene-9-carboxylic acid (371111-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 4-methylmorpholine; isobutyl chloroformate / CH₂Cl₂ / -10 - -5 °C

1.2: 53 percent / 4-methylmorpholine / CH₂Cl₂; dimethylformamide / 1 h / 20 °C

2.1: 96 percent / HCl / dioxane / 2 h / 20 °C

With 4-methyl-morpholine; hydrogenchloride; isobutyl chloroformate; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jm0489556

upstream raw materials:

Boc-p-chloro-L-Phe-OH

[S,S]-2-(2-tert-butoxycarbonylamino-2-cyclohexylacetylamino)-3-(3-hydroxyphenyl)propionic acid methyl ester

N-(tert-butoxycarbonyl)-L-cyclohexylglycine

methyl (2S)-2-amino-3-(3-hydroxyphenyl)propanoate hydrochloride

Downstream raw materials:

(S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester

{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetic acid benzyl ester

{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetic acid benzyl ester

(S)-(2-{3-[((9S,12S,15S)-15-tert-Butoxycarbonylamino-12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carbonyl)-amino]-2-hydroxy-hexanoylamino}-acetylamino)-phenyl-acetic acid benzyl ester

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