10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13S-carboxylic acid benzyl ester

Base Information

• Chemical Name: 10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13S-carboxylic acid benzyl ester
• CAS No.: 180078-22-2
• Molecular Formula: C₂₇H₃₄N₂O₅
• Molecular Weight: 466.577

Synonyms:10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13S-carboxylic acid benzyl ester

Chemical Property of 10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13S-carboxylic acid benzyl ester

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Technology Process of 10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13S-carboxylic acid benzyl ester

There total 6 articles about 10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-13S-carboxylic acid benzyl 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:

(S)-3-(4-Hydroxy-phenyl)-2-[(S)-2-(6-iodo-hexanoylamino)-3-methyl-butyrylamino]-propionic acid benzyl ester (437754-03-5) → 10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-13S-carboxylic acid benzyl ester (180078-22-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/ja0256461

Reference yield:

t-Boc-L-valine (13734-41-3) → 10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-13S-carboxylic acid benzyl ester (180078-22-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: isobutyl chloroformate; N-methyl morpholine / tetrahydrofuran / 0.08 h / -10 °C

1.2: 98 percent / HOBt; N-methyl morpholine / CH₂Cl₂; tetrahydrofuran / 3 h / 20 °C

2.1: TFA / 0.25 h

3.1: 5.1 g / aq. K₂CO₃ / tetrahydrofuran / 0.5 h / 20 °C / pH 9

4.1: NaI / acetone / 20 °C

5.1: 580 mg / K₂CO₃ / dimethylformamide / 20 °C

With 4-methyl-morpholine; potassium carbonate; trifluoroacetic acid; sodium iodide; isobutyl chloroformate; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja0256461

Reference yield:

L-tyrosine benzyl ester (42406-77-9) → 10S-isopropyl-8,11-dioxo-2-oxa-9,12-diaza-bicyclo[13.2.2]nonadeca-1(18),15(19),16-triene-13S-carboxylic acid benzyl ester (180078-22-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: isobutyl chloroformate; N-methyl morpholine / tetrahydrofuran / 0.08 h / -10 °C

1.2: 98 percent / HOBt; N-methyl morpholine / CH₂Cl₂; tetrahydrofuran / 3 h / 20 °C

2.1: TFA / 0.25 h

3.1: 5.1 g / aq. K₂CO₃ / tetrahydrofuran / 0.5 h / 20 °C / pH 9

4.1: NaI / acetone / 20 °C

5.1: 580 mg / K₂CO₃ / dimethylformamide / 20 °C

With 4-methyl-morpholine; potassium carbonate; trifluoroacetic acid; sodium iodide; isobutyl chloroformate; In tetrahydrofuran; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja0256461

upstream raw materials:

(S)-3-(4-Hydroxy-phenyl)-2-[(S)-2-(6-iodo-hexanoylamino)-3-methyl-butyrylamino]-propionic acid benzyl ester

t-Boc-L-valine

L-tyrosine benzyl ester

H-Val-Tyr-OBzl

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