(8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁹⁾,3,5,7⁽²⁰⁾,15,17-hexaene-8-carboxylic acid ethyl ester

Base Information

• Chemical Name: (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁹⁾,3,5,7⁽²⁰⁾,15,17-hexaene-8-carboxylic acid ethyl ester
• CAS No.: 143145-51-1
• Molecular Formula: C₃₄H₃₉N₃O₁₀
• Molecular Weight: 649.698

Synonyms:(8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁹⁾,3,5,7⁽²⁰⁾,15,17-hexaene-8-carboxylic acid ethyl ester

Chemical Property of (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁹⁾,3,5,7⁽²⁰⁾,15,17-hexaene-8-carboxylic acid ethyl ester

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Technology Process of (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁹⁾,3,5,7⁽²⁰⁾,15,17-hexaene-8-carboxylic acid ethyl ester

There total 25 articles about (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁹⁾,3,5,7⁽²⁰⁾,15,17-hexaene-8-carboxylic acid ethyl ester 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: 50.0%

N-D-tyrosyl-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>amino-<(pentafluorophenoxy)carbonyl>methyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester hydrochloride (143171-02-2) → (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(19),3,5,7(20),15,17-hexaene-8-carboxylic acid ethyl ester (143145-51-1)

Guidance literature:

With triethylamine; In 1,4-dioxane; at 90 ℃; for 16h;

DOI:10.1021/jo00046a031

Reference yield:

3,5-Dihydroxybenzoic acid (99-10-5) → (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(19),3,5,7(20),15,17-hexaene-8-carboxylic acid ethyl ester (143145-51-1)

Guidance literature:

Multi-step reaction with 23 steps

1: 96 percent / conc. H₂SO₄ / 5 h / Heating

2: 65 percent / K₂CO₃, Bu₄NI / acetone / 3 h / Heating

3: 1) NaH / 1) DMF, r.t., 0.5 h, 2) 90 deg C, 3 h

4: 95 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 1) DIBALH, 2) 1N HCl / 1) a) CH₂Cl₂, -78 deg C, 0.5 h, 2) MeOH, 0 deg C, 0.5 h

6: 86 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 0 °C

7: CHCl₃ / 5 h / Ambient temperature

8: methanol / 3 h

9: 90 percent / ethereal HCl / 5 h / Ambient temperature

10: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / 0 °C / 1) CH₂Cl₂, MeOH, 0 deg C, 5 min, 2) phosphate buffer pH 7, r.t., 0.5 h

11: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

12: 1) 1-hydroxybenzotriazole hydrate, 1,3-dicyclohexylcarbodiimide / 1) DMF, 0 deg C, 30 min, 2) DMF, 0 deg C to r.t., 1,5 h

13: 85 percent / mercuric oxide, mercuric chloride / acetonitrile; H₂O / 2 h / Ambient temperature

14: CHCl₃ / 24 h / Ambient temperature

15: CHCl₃ / 24 h / Ambient temperature

16: 52 percent / ethereal HCl / CHCl₃ / 3 h / Ambient temperature

17: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / ice-cold

18: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

19: 80 percent / CH₂Cl₂ / 3 h / Ambient temperature

20: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

21: 80 percent / 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 1 h / Ambient temperature

22: aqueous HCl, H₂ / palladium on charcoal / tetrahydrofuran / 3 h / Ambient temperature

23: 50 percent / triethylamine / dioxane / 16 h / 90 °C

With lead(IV) acetate; hydrogenchloride; methanol; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; water; acetone; acetonitrile;

DOI:10.1021/jo00046a031

Reference yield:

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → (8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(19),3,5,7(20),15,17-hexaene-8-carboxylic acid ethyl ester (143145-51-1)

Guidance literature:

Multi-step reaction with 22 steps

1: 65 percent / K₂CO₃, Bu₄NI / acetone / 3 h / Heating

2: 1) NaH / 1) DMF, r.t., 0.5 h, 2) 90 deg C, 3 h

3: 95 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 1) DIBALH, 2) 1N HCl / 1) a) CH₂Cl₂, -78 deg C, 0.5 h, 2) MeOH, 0 deg C, 0.5 h

5: 86 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 0 °C

6: CHCl₃ / 5 h / Ambient temperature

7: methanol / 3 h

8: 90 percent / ethereal HCl / 5 h / Ambient temperature

9: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / 0 °C / 1) CH₂Cl₂, MeOH, 0 deg C, 5 min, 2) phosphate buffer pH 7, r.t., 0.5 h

10: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

11: 1) 1-hydroxybenzotriazole hydrate, 1,3-dicyclohexylcarbodiimide / 1) DMF, 0 deg C, 30 min, 2) DMF, 0 deg C to r.t., 1,5 h

12: 85 percent / mercuric oxide, mercuric chloride / acetonitrile; H₂O / 2 h / Ambient temperature

13: CHCl₃ / 24 h / Ambient temperature

14: CHCl₃ / 24 h / Ambient temperature

15: 52 percent / ethereal HCl / CHCl₃ / 3 h / Ambient temperature

16: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / ice-cold

17: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

18: 80 percent / CH₂Cl₂ / 3 h / Ambient temperature

19: 90 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h / Ambient temperature

20: 80 percent / 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 1 h / Ambient temperature

21: aqueous HCl, H₂ / palladium on charcoal / tetrahydrofuran / 3 h / Ambient temperature

22: 50 percent / triethylamine / dioxane / 16 h / 90 °C

With lead(IV) acetate; hydrogenchloride; methanol; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1-hydroxybenzotriazol-hydrate; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; mercury dichloride; mercury(II) oxide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; chloroform; water; acetone; acetonitrile;

DOI:10.1021/jo00046a031

upstream raw materials:

N-D-tyrosyl-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>amino-<(pentafluorophenoxy)carbonyl>methyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester hydrochloride

1-carbomethoxy-3,5-dihydroxybenzene

3,5-Dihydroxybenzoic acid

3-hydroxy-5-methoxy-benzoic acid methyl ester

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