methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-9-carboxylate]

Base Information

• Chemical Name: methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-9-carboxylate]
• CAS No.: 371111-47-6
• Molecular Formula: C₂₈H₃₄N₂O₅
• Molecular Weight: 478.588

Synonyms:methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-9-carboxylate]

Chemical Property of methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-9-carboxylate]

Chemical Property:

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Technology Process of methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-9-carboxylate]

There total 4 articles about methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-9-carboxylate] 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) → methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaene-9-carboxylate] (371111-47-6)

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) → methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaene-9-carboxylate] (371111-47-6)

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) → methyl [12S,9S]-[12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.13,7]tricosa-1(21),3(23),4,6,18(22),19-hexaene-9-carboxylate] (371111-47-6)

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:

4-(4-chlorophenyl)butanoic acid

[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:

[12S,9S]-(2-{3-[(12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3⁽²³⁾,4,6,18⁽²²⁾,19-hexaene-9-carbonyl)amino]-2-hydroxyhexanoylamino}acetylamino)phenylacetic acid tert-butyl ester

(S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[16.2.2.1^3,7]tricosa-1⁽²¹⁾,3,5,7⁽²³⁾,18⁽²²⁾,19-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester

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